Search for "phosphotungstic acid" in Full Text gives 10 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162
Graphical Abstract
Scheme 1: Mechanism of the GBB reaction.
Scheme 2: Comparison of the performance of Sc(OTf)3 with some RE(OTf)3 in a model GBB reaction. Conditions: a...
Scheme 3: Comparison of the performance of various Brønsted acid catalysts in the synthesis of GBB adduct 6. ...
Scheme 4: Synthesis of Brønsted acidic ionic liquid catalyst 7. Conditions: a) neat, 60 °C, 24 h; b) TfOH, DC...
Scheme 5: Aryliodonium derivatives as organic catalysts in the GBB reaction. In the box the proposed binding ...
Scheme 6: DNA-encoded GBB reaction in micelles made of amphiphilic polymer 13. Conditions: a) 13 (50 equiv), ...
Scheme 7: GBB reaction catalyzed by cyclodextrin derivative 14. Conditions: a) 14 (1 mol %), water, 100 °C, 4...
Scheme 8: Proposed mode of activation of CALB. a) activation of the substrates; b) activation of the imine; c...
Scheme 9: One-pot GBB reaction–Suzuki coupling with a bifunctional hybrid biocatalyst. Conditions: a) Pd(0)-C...
Scheme 10: GBB reaction employing 5-HMF (23) as carbonyl component. Conditions: a) TFA (20 mol %), EtOH, 60 °C...
Scheme 11: GBB reaction with β-C-glucopyranosyl aldehyde 26. Conditions: a) InCl3 (20 mol %), MeOH, 70 °C, 2–3...
Scheme 12: GBB reaction with diacetylated 5-formyldeoxyuridine 29, followed by deacetylation of GBB adduct 30....
Scheme 13: GBB reaction with glycal aldehydes 32. Conditions: a) HFIP, 25 °C, 2–4 h.
Scheme 14: Vilsmeier–Haack formylation of 6-β-acetoxyvouacapane (34) and subsequent GBB reaction. Conditions: ...
Scheme 15: GBB reaction of 4-formlyl-PCP 37. Conditions: a) HOAc or HClO4, MeOH/DCM (2:3), rt, 3 d.
Scheme 16: GBB reaction with HexT-aldehyde 39. Conditions: a) 39 (20 nmol) and amidine (20 μmol), MeOH, rt, 6 ...
Scheme 17: GBB reaction of 2,4-diaminopirimidine 41. Conditions: a) Sc(OTf)3 (20 mol %), MeCN, 120 °C (MW), 1 ...
Scheme 18: Synthesis of N-edited guanine derivatives from 3,6-diamine-1,2,4-triazin-5-one 44. Conditions: a) S...
Scheme 19: Synthesis of 2-aminoimidazoles 49 by a Mannich-3CR followed by a one-pot intramolecular oxidative a...
Scheme 20: On DNA Suzuki–Miyaura reaction followed by GBB reaction. Conditions: a) CsOH, sSPhos-Pd-G2; b) AcOH...
Scheme 21: One-pot cascade synthesis of 5-iminoimidazoles. Conditions: a) Na2SO4, DMF, 220 °C (MW).
Scheme 22: GBB reaction of 5-amino-1H-imidazole-4-carbonile 57. Conditions: a) HClO4 (5 mol %), MeOH, rt, 24 h....
Scheme 23: One-pot cascade synthesis of indole-imidazo[1,2,a]pyridine hybrids. In blue the structural motif in...
Scheme 24: One-pot cascade synthesis of fused polycyclic indoles 67 or 69 from indole-3-carbaldehyde. Conditio...
Scheme 25: One-pot cascade synthesis of linked- and bridged polycyclic indoles from indole-2-carbaldehyde (70)...
Scheme 26: One-pot cascade synthesis of pentacyclic dihydroisoquinolines (X = N or CH). In blue the structural...
Scheme 27: One-pot stepwise synthesis of imidazopyridine-fused benzodiazepines 85. Conditions: a) p-TsOH (20 m...
Scheme 28: One-pot stepwise synthesis of benzoxazepinium-fused imidazothiazoles 89. Conditions: a) Yb(OTf)3 (2...
Scheme 29: One-pot stepwise synthesis of fused imidazo[4,5,b]pyridines 95. Conditions: a) HClO4, MeOH, rt, ove...
Scheme 30: Synthesis of heterocyclic polymers via the GBB reaction. Conditions: a) p-TsOH, EtOH, 70 °C, 24 h.
Scheme 31: One-pot multicomponent reaction towards the synthesis of covalent organic frameworks via the GBB re...
Scheme 32: One-pot multicomponent reaction towards the synthesis of covalent organic frameworks via the GBB re...
Scheme 33: GBB-like multicomponent reaction towards the synthesis of benzothiazolpyrroles (X = S) and benzoxaz...
Scheme 34: GBB-like multicomponent reaction towards the formation of imidazo[1,2,a]pyridines. Conditions: a) I2...
Scheme 35: Post-functionalization of GBB products via Ugi reaction. Conditions a) HClO4, DMF, rt, 24 h; b) MeO...
Scheme 36: Post-functionalization of GBB products via Click reaction. Conditions: a) solvent-free, 150 °C, 24 ...
Scheme 37: Post-functionalization of GBB products via cascade alkyne–allene isomerization–intramolecular nucle...
Scheme 38: Post-functionalization of GBB products via metal-catalyzed intramolecular N-arylation. In red and b...
Scheme 39: Post-functionalization of GBB products via isocyanide insertion (X = N or CH). Conditions: a) HClO4...
Scheme 40: Post-functionalization of GBB products via intramolecular nucleophilic addition to nitriles. Condit...
Scheme 41: Post-functionalization of GBB products via Pictet–Spengler cyclization. Conditions: a) 4 N HCl/diox...
Scheme 42: Post-functionalization of GBB products via O-alkylation. Conditions: a) TFA (20 mol %), EtOH, 120 °...
Scheme 43: Post-functionalization of GBB products via macrocyclization (X = -CH2CH2O-, -CH2-, -(CH2)4-). Condi...
Figure 1: Antibacterial activity of GBB-Ugi adducts 113 on both Gram-negative and Gram-positive strains.
Scheme 44: GBB multicomponent reaction using trimethoprim as the precursor. Conditions: a) Yb(OTf)3 or Y(OTf)3...
Figure 2: Antibacterial activity of GBB adducts 152 against MRSA and VRE; NA = not available.
Figure 3: Antibacterial activity of GBB adduct 153 against Leishmania amazonensis promastigotes and amastigot...
Figure 4: Antiviral and anticancer evaluation of the GBB adducts 154a and 154b. In vitro antiproliferative ac...
Figure 5: Anticancer activity of the GBB-furoxan hybrids 145b, 145c and 145d determined through antiprolifera...
Scheme 45: Synthesis and anticancer activity of the GBB-gossypol conjugates. Conditions: a) Sc(OTf)3 (10 mol %...
Figure 6: Anticancer activity of polyheterocycles 133a and 136a against human neuroblastoma. Clonogenic assay...
Figure 7: Development of GBB-adducts 158a and 158b as PD-L1 antagonists. HTRF assays were carried out against...
Figure 8: Development of imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrazines as TDP1 inhibitors. The SMM meth...
Figure 9: GBB adducts 164a–c as anticancer through in vitro HDACs inhibition assays. Additional cytotoxic ass...
Figure 10: GBB adducts 165, 166a and 166b as anti-inflammatory agents through HDAC6 inhibition; NA = not avail...
Scheme 46: GBB reaction of triphenylamine 167. Conditions: a) NH4Cl (10 mol %), MeOH, 80 °C (MW), 1 h.
Scheme 47: 1) Modified GBB-3CR. Conditions: a) TMSCN (1.0 equiv), Sc(OTf)3 (0.2 equiv), MeOH, 140 °C (MW), 20 ...
Scheme 48: GBB reaction to assemble imidazo-fused heterocycle dimers 172. Conditions: a) Sc(OTf)3 (20 mol %), ...
Figure 11: Model compounds 173 and 174, used to study the acid/base-triggered reversible fluorescence response...
Beilstein J. Org. Chem. 2024, 20, 628–637, doi:10.3762/bjoc.20.55
Graphical Abstract
Figure 1: Selected examples of commercial drugs containing the imidazo[1,2-a]pyridine core [13].
Figure 2: Examples of application of HPW as catalyst in the synthesis of heterocyclic compounds through multi...
Scheme 1: a) Reported phosphomolybdic acid-catalyzed synthesis of imidazo[1,2-a]pyridines via GBB-3CR. b) Att...
Scheme 2: Substrate scope of the HPW-catalyzed GBB reactions using a range of aromatic/heteroaromatic aldehyd...
Scheme 3: Substrate scope of the HPW-catalyzed GBB reaction using aliphatic aldehydes. Reaction conditions: 2...
Scheme 4: Unsuccessful substrates for the HPW-catalyzed GBB-3CR for the synthesis of imidazo[1,2-a]pyridines.
Scheme 5: 10-Fold scale-up of the HPW-catalyzed GBB reaction (5.0 mmol) between 2-aminopyridine (1a), 4-nitro...
Scheme 6: Plausible reaction mechanism for the HPW-catalyzed GBB reaction.
Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53
Graphical Abstract
Figure 1: Potential classification of plastic recycling processes. The area covered by the present review is ...
Figure 2: EG produced during glycolytic depolymerisation of PET using DEG + DPG as solvent and titanium(IV) n...
Scheme 1: Simplified representation of the conversion of 1,4-PBD to C16–C44 macrocycles using Ru metathesis c...
Figure 3: Main added-value monomers obtainable by catalytic depolymerisation of PET via chemolytic methods.
Scheme 2: Hydrogenolytic depolymerisation of PET by ruthenium complexes.
Scheme 3: Depolymerisation of PET via catalytic hydrosilylation by Ir(III) pincer complex.
Scheme 4: Catalytic hydrolysis (top) and methanolysis (bottom) reactions of PET.
Scheme 5: Depolymerisation of PET by glycolysis with ethylene glycol.
Figure 4: Glycolysis of PET: evolution of BHET yield over time, with and without zinc acetate catalyst (196 °...
Scheme 6: Potential activated complex for the glycolysis reaction of PET catalysed by metallated ILs and evol...
Scheme 7: One-pot, two-step process for PET repurposing via chemical recycling.
Scheme 8: Synthetic routes to PLA.
Scheme 9: Structures of the zinc molecular catalysts used for PLA-methanolysis in various works. a) See [265], b) ...
Scheme 10: Depolymerisation of PLLA by Zn–N-heterocyclic carbene complex.
Scheme 11: Salalen ligands.
Scheme 12: Catalytic hydrogenolysis of PLA.
Scheme 13: Catalytic hydrosilylation of PLA.
Scheme 14: Hydrogenative depolymerisation of PBT and PCL by molecular Ru catalysts.
Scheme 15: Glycolysis reaction of PCT by diethylene glycol.
Scheme 16: Polymerisation–depolymerisation cycle of 3,4-T6GBL.
Scheme 17: Polymerisation–depolymerisation cycle of 2,3-HDB.
Scheme 18: Hydrogenative depolymerisation of PBPAC by molecular Ru catalysts.
Scheme 19: Catalytic hydrolysis (top), alcoholysis (middle) and aminolysis (bottom) reactions of PBPAC.
Scheme 20: Hydrogenative depolymerisation of PPC (top) and PEC (bottom) by molecular Ru catalysts.
Scheme 21: Polymerisation-depolymerisation cycle of BEP.
Scheme 22: Hydrogenolysis of polyamides using soluble Ru catalysts.
Scheme 23: Catalytic depolymerisation of epoxy resin/carbon fibres composite.
Scheme 24: Depolymerisation of polyethers with metal salt catalysts and acyl chlorides.
Scheme 25: Proposed mechanism for the iron-catalysed depolymerisation reaction of polyethers. Adapted with per...
Beilstein J. Org. Chem. 2020, 16, 2862–2869, doi:10.3762/bjoc.16.235
Graphical Abstract
Scheme 1: The classical Hantzsch synthesis between benzaldehyde (1a), ethyl acetoacetate (2), and ammonium ac...
Figure 1: Optimization trials with the selected solid catalysts.
Figure 2: Graphical representation of the results obtained in the reusability test.
Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186
Graphical Abstract
Figure 1: Representation of corannulene (1) and sumanene (2), the subunits of fullerene (C60).
Scheme 1: Mehta’s unsuccessful effort for the synthesis of sumanene scaffold 2.
Scheme 2: First synthesis of sumanene 2 by Sakurai et al. from norbornadiene 10.
Scheme 3: Synthesis of trimethylsumanene 28 from easily accessible norbornadiene (10).
Scheme 4: Generation of anions 29–31 and the preparation of tris(trimethylsilyl)sumanene 32.
Scheme 5: Synthesis of tri- and hexa-substituted sumanene derivatives.
Scheme 6: Synthesis of bowl-shaped π-extended sumanene derivatives 37a–f.
Scheme 7: Synthesis of monooxasumanene 38, trioxosumanene 40 along with imination of them.
Scheme 8: Synthesis of trimethylsumanenetrione 46 and exo-functionalized products 45a,b.
Scheme 9: Synthesis of bisumanenylidene 47 and sumanene dimer 48 from 2.
Scheme 10: The mono-substitution of 2 to generate diverse mono-sumanene derivatives 49a–d.
Scheme 11: Synthesis of sumanene building block 53 useful for further extension.
Scheme 12: Synthesis of hexafluorosumanene derivative 55 by Sakurai and co-workers.
Scheme 13: Preparation of sumanene-based carbene 60 and its reaction with cyclohexane.
Scheme 14: Barton–Kellogg reaction for the synthesis of sterically hindered alkenes.
Scheme 15: Synthesis of hydroxysumanene 68 by employing Baeyer–Villiger oxidation.
Scheme 16: Synthesis of sumanene derivatives having functionality at an internal carbon.
Scheme 17: Mechanism for nucleophilic substitution reaction at the internal carbon.
Scheme 18: Synthesis of diverse monosubstituted sumanene derivatives.
Scheme 19: Synthesis of di- and trisubstituted sumanene derivatives from sumanene (2).
Scheme 20: Preparation of monochlorosumanene 88 and hydrogenation of sumanene (2).
Scheme 21: The dimer 90 and bissumanenyl 92 achieved from halosumannes.
Scheme 22: Pyrenylsumanene 93 involving the Suzuki-coupling as a key transformation.
Scheme 23: Synthesis of various hexaarylsumanene derivatives using the Suzuki-coupling reaction.
Scheme 24: Synthesis of hexasubstituted sumanene derivatives 96 and 97.
Scheme 25: Synthesis of thioalkylsumanenes via an aromatic nucleophilic substitution reaction.
Scheme 26: Synthesis of tris(ethoxycarbonylethenyl)sumanene derivative 108.
Scheme 27: Synthesis of ferrocenyl-based sumanene derivatives.
Scheme 28: Synthesis of sumanenylferrocene architectures 118 and 119 via Negishi coupling.
Scheme 29: Diosmylation and the synthesis of phenylboronate ester 121 of sumanene.
Scheme 30: Synthesis of the iron-complex of sumanene.
Scheme 31: Synthesis of tri- and mononuclear sumanenyl zirconocene complexes.
Scheme 32: Synthesis of [CpRu(η6-sumanene)]PF6.
Scheme 33: Preparation of sumanene-based porous coordination networks 127 (spherical tetramer units) and 128 (...
Scheme 34: Synthesis of sumanenylhafnocene complexes 129 and 130.
Scheme 35: Synthesis of 134 and 135 along with PdII coordination complex 136.
Scheme 36: Synthesis of alkali metals sumanene complex K7(C21H102−)2(C21H93−)·8THF (137) containing di- and tr...
Scheme 37: The encapsulation of a Cs+ ion between two sumanenyl anions.
Scheme 38: Synthesis of monothiasumanene 140 and dithiasumanene 141 from 139.
Scheme 39: Synthesis of trithiasumanene 151 by Otsubo and his co-workers.
Scheme 40: Synthesis of trithiasumanene derivatives 155 and 156.
Scheme 41: Synthetic route towards hexathiolated trithiasumanenes 158.
Scheme 42: Synthesis of triselenasumanene 160 by Shao and teammates.
Scheme 43: Synthesis of tritellurasumanene derivatives from triphenylene skeletons.
Scheme 44: Synthesis of pyrazine-fused sumanene architectures through condensation reaction.
Scheme 45: Treatment of the trichalcogenasumanenes with diverse oxidative reagents.
Scheme 46: Ring-opening reaction with H2O2 and oxone of heterasumanenes 178 and 179.
Scheme 47: Synthesis of polycyclic compounds from sumanene derivatives.
Scheme 48: Synthesis of diimide-based heterocycles reported by Shao’s and co-workers.
Scheme 49: Synthesis of pristine trichalcogenasumanenes, 151, 205, and 206.
Scheme 50: Synthesis of trichalcogenasumanenes via hexaiodotriphenylene precursor 208.
Scheme 51: Synthesis of trisilasumanenes 214 and 215.
Scheme 52: Synthesis of trisilasumanene derivatives 218 and 219.
Scheme 53: Synthesis of novel trigermasumanene derivative 223.
Scheme 54: An attempt towards the synthesis of tristannasumanene derivative 228.
Scheme 55: Synthesis of triphosphasumanene trisulfide 232 from commercially available 229.
Scheme 56: The doping of sumanene derivatives with chalcogens (S, Se, Te) and phosphorus.
Scheme 57: Synthesis of heterasumanene containing three different heteroatoms.
Scheme 58: Synthesis of trichalcogenasumanene derivatives 240 and 179.
Scheme 59: Preparation of trichalcogenasumanenes 245 and 248.
Scheme 60: Design and synthesis of trichalcogenasumanene derivatives 252 and 178.
Scheme 61: Synthesis of spirosumanenes 264–269 and non-spiroheterasumanenes 258–263.
Scheme 62: Synthesis of sumanene-type hetero polycyclic compounds.
Scheme 63: Synthesis of triazasumanenes 288 and its sulfone congener 287.
Scheme 64: Synthesis of C3-symmetric chiral triaryltriazasumanenes via cross-coupling reaction.
Scheme 65: Synthesis of mononaphthosumanene 293 using Suzuki coupling as a key step.
Scheme 66: Synthesis of di- and trinaphthosumanene derivatives 302–304.
Scheme 67: Synthesis of hemifullerene skeletons by Hirao’s group.
Scheme 68: Design and construction of C70 fragment from a C60 sumanene fragment.
Beilstein J. Org. Chem. 2020, 16, 1713–1721, doi:10.3762/bjoc.16.143
Graphical Abstract
Scheme 1: Conversion of cellulose to isosorbide.
Scheme 2: Combination of mineral acids or heteropolyacids and a supported metal catalyst to produce isosorbid...
Scheme 3: Conversion of sorbitol to isosorbide via the formation of sorbitans.
Scheme 4: Conversion of cellulose to isosorbide in the presence of heteropolyacids and metal-supported cataly...
Scheme 5: Summary of the results obtained in one-pot one step processes [21-25].
Scheme 6: Conversion of (ligno)cellulose to isosorbide in the presence of Amberlyt 70 and a Ru/C catalyst [26,27].
Scheme 7: Use of Ru-supported on mesoporous nobium phosphate (mNbPO) for the synthesis of isosorbide from cel...
Beilstein J. Org. Chem. 2017, 13, 874–882, doi:10.3762/bjoc.13.88
Graphical Abstract
Figure 1: Expression of GFP-tagged GAT1 in infected insect cells. (A) Flow cytometry analysis of GAT1/GFP in ...
Figure 2: Protein fingerprinting. (A) Coomassie Blue staining of the GAT1/GFP protein from infected Sf9 cells...
Figure 3: Isolation of the GAT1/GFP fusion protein from Sf9 cells by mAb-GFP-conjugated affinity column chrom...
Figure 4: Purification of the GAT1/GFP fusion protein from Sf9 cells by SE-FPLC. (A) Elution profile of GAT1/...
Figure 5: Characterization of the GAT1/GFP fusion protein after SE-FPLC. (A) Elution profile of GAT1/GFP prot...
Beilstein J. Org. Chem. 2016, 12, 2173–2180, doi:10.3762/bjoc.12.207
Graphical Abstract
Scheme 1: Synthesis of levulinic acid from ligno-cellulosic feedstocks and its principal uses to access fine ...
Figure 1: Anchoring methodologies: a) impregnation; b) covalent binding.
Figure 2: Activity of the supported sulfonic acid catalyst within the first six cycles. Reaction conditions: ...
Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121
Graphical Abstract
Scheme 1: The Biginelli condensation.
Scheme 2: The Biginelli reaction of β-ketophosphonates catalyzed by ytterbium triflate.
Scheme 3: Trimethylchlorosilane-mediated Biginelli reaction of diethyl (3,3,3-trifluoropropyl-2-oxo)phosphona...
Scheme 4: Biginelli reaction of dialkyl (3,3,3-trifluoropropyl-2-oxo)phosphonate with trialkyl orthoformates ...
Scheme 5: p-Toluenesulfonic acid-promoted Biginelli reaction of β-ketophosphonates, aryl aldehydes and urea.
Scheme 6: General Kabachnik–Fields reaction for the synthesis of α-aminophosphonates.
Scheme 7: Phthalocyanine–AlCl catalyzed Kabachnik–Fields reaction of N-Boc-piperidin-4-one with diethyl phosp...
Scheme 8: Kabachnik–Fields reaction of isatin with diethyl phosphite and benzylamine.
Scheme 9: Magnetic Fe3O4 nanoparticle-supported phosphotungstic acid-catalyzed Kabachnik–Fields reaction of i...
Scheme 10: The Mg(ClO4)2-catalyzed Kabachnik–Fields reaction of 1-tosylpiperidine-4-one.
Scheme 11: An asymmetric version of the Kabachnik–Fields reaction for the synthesis of α-amino-3-piperidinylph...
Scheme 12: A classical Kabachnik–Fields reaction followed by an intramolecular ring-closing reaction for the s...
Scheme 13: Synthesis of (S)-piperidin-2-phosphonic acid through an asymmetric Kabachnik–Fields reaction.
Scheme 14: A modified diastereoselective Kabachnik–Fields reaction for the synthesis of isoindolin-1-one-3-pho...
Scheme 15: A microwave-assisted Kabachnik–Fields reaction toward isoindolin-1-ones.
Scheme 16: The synthesis of 3-arylmethyleneisoindolin-1-ones through a Horner–Wadsworth–Emmons reaction of Kab...
Scheme 17: An efficient one-pot method for the synthesis of ethyl (2-alkyl- and 2-aryl-3-oxoisoindolin-1-yl)ph...
Scheme 18: FeCl3 and PdCl2 co-catalyzed three-component reaction of 2-alkynylbenzaldehydes, anilines, and diet...
Scheme 19: Three-component reaction of 6-methyl-3-formylchromone (75) with hydrazine derivatives or hydroxylam...
Scheme 20: Three-component reaction of 6-methyl-3-formylchromone (75) with thiourea, guanidinium carbonate or ...
Scheme 21: Three-component reaction of 6-methyl-3-formylchromone (75) with 1,4-bi-nucleophiles in the presence...
Scheme 22: One-pot three-component reaction of 2-alkynylbenzaldehydes, amines, and diethyl phosphonate.
Scheme 23: Lewis acid–surfactant combined catalysts for the one-pot three-component reaction of 2-alkynylbenza...
Scheme 24: Lewis acid catalyzed cyclization of different Kabachnik–Fields adducts.
Scheme 25: Three-component synthesis of N-arylisoquinolone-1-phosphonates 119.
Scheme 26: CuI-catalyzed three-component tandem reaction of 2-(2-formylphenyl)ethanones with aromatic amines a...
Scheme 27: Synthesis of 1,5-benzodiazepin-2-ylphosphonates via ytterbium chloride-catalyzed three-component re...
Scheme 28: FeCl3-catalyzed four-component reaction for the synthesis of 1,5-benzodiazepin-2-ylphosphonates.
Scheme 29: Synthesis of indole bisphosphonates through a modified Kabachnik–Fields reaction.
Scheme 30: Synthesis of heterocyclic bisphosphonates via Kabachnik–Fields reaction of triethyl orthoformate.
Scheme 31: A domino Knoevenagel/phospha-Michael process for the synthesis of 2-oxoindolin-3-ylphosphonates.
Scheme 32: Intramolecular cyclization of phospha-Michael adducts to give dihydropyridinylphosphonates.
Scheme 33: Synthesis of fused phosphonylpyrans via intramolecular cyclization of phospha-Michael adducts.
Scheme 34: InCl3-catalyzed three-component synthesis of (2-amino-3-cyano-4H-chromen-4-yl)phosphonates.
Scheme 35: Synthesis of phosphonodihydropyrans via a domino Knoevenagel/hetero-Diels–Alder process.
Scheme 36: Multicomponent synthesis of phosphonodihydrothiopyrans via a domino Knoevenagel/hetero-Diels–Alder ...
Scheme 37: One-pot four-component synthesis of 1,2-dihydroisoquinolin-1-ylphosphonates under multicatalytic co...
Scheme 38: CuI-catalyzed four-component reactions of methyleneaziridines towards alkylphosphonates.
Scheme 39: Ruthenium–porphyrin complex-catalyzed three-component synthesis of aziridinylphosphonates and its p...
Scheme 40: Copper(I)-catalyzed three-component reaction towards 1,2,3-triazolyl-5-phosphonates.
Scheme 41: Three-component reaction of acylphosphonates, isocyanides and dialkyl acetylenedicarboxylate to aff...
Scheme 42: Synthesis of (4-imino-3,4-dihydroquinazolin-2-yl)phosphonates via an isocyanide-based three-compone...
Scheme 43: Silver-catalyzed three-component synthesis of (2-imidazolin-4-yl)phosphonates.
Scheme 44: Three-component synthesis of phosphonylpyrazoles.
Scheme 45: One-pot three-component synthesis of 3-carbo-5-phosphonylpyrazoles.
Scheme 46: A one-pot two-step method for the synthesis of phosphonylpyrazoles.
Scheme 47: A one-pot method for the synthesis of (5-vinylpyrazolyl)phosphonates.
Scheme 48: Synthesis of 1H-pyrrol-2-ylphosphonates via the [3 + 2] cycloaddition of phosphonate azomethine yli...
Scheme 49: Three-component synthesis of 1H-pyrrol-2-ylphosphonates.
Scheme 50: The classical Reissert reaction.
Scheme 51: One-pot three-component synthesis of N-phosphorylated isoquinolines.
Scheme 52: One-pot three-component synthesis of 1-acyl-1,2-dihydroquinoline-2-phosphonates and 2-acyl-1,2-dihy...
Scheme 53: Three-component reaction of pyridine derivatives with ethyl propiolate and dialkyl phosphonates.
Scheme 54: Three-component reactions for the phosphorylation of benzothiazole and isoquinoline.
Scheme 55: Three-component synthesis of diphenyl [2-(aminocarbonyl)- or [2-(aminothioxomethyl)-1,2-dihydroisoq...
Scheme 56: Three-component stereoselective synthesis of 1,2-dihydroquinolin-2-ylphosphonates and 1,2-dihydrois...
Scheme 57: Diphosphorylation of diazaheterocyclic compounds via a tandem 1,4–1,2 addition of dimethyl trimethy...
Scheme 58: Multicomponent reaction of alkanedials, acetamide and acetyl chloride in the presence of PCl3 and a...
Scheme 59: An oxidative domino three-component synthesis of polyfunctionalized pyridines.
Scheme 60: A sequential one-pot three-component synthesis of polysubstituted pyrroles.
Scheme 61: Three-component decarboxylative coupling of proline with aldehydes and dialkyl phosphites for the s...
Scheme 62: Three-component domino aza-Wittig/phospha-Mannich sequence for the phosphorylation of isatin deriva...
Scheme 63: Stereoselective synthesis of phosphorylated trans-1,5-benzodiazepines via a one-pot three-component...
Scheme 64: One-pot three-component synthesis of phosphorylated 2,6-dioxohexahydropyrimidines.
Beilstein J. Org. Chem. 2014, 10, 34–114, doi:10.3762/bjoc.10.6
Graphical Abstract
Figure 1: Five and six-membered cyclic peroxides.
Figure 2: Artemisinin and semi-synthetic derivatives.
Scheme 1: Synthesis of 3-hydroxy-1,2-dioxolanes 3a–c.
Scheme 2: Synthesis of dioxolane 6.
Scheme 3: Photooxygenation of oxazolidines 7a–d with formation of spiro-fused oxazolidine-containing dioxolan...
Scheme 4: Oxidation of cyclopropanes 10a–e and 11a–e with preparation of 1,2-dioxolanes 12a–e.
Scheme 5: VO(acac)2-catalyzed oxidation of silylated bicycloalkanols 13a–c.
Scheme 6: Mn(II)-catalyzed oxidation of cyclopropanols 15a–g.
Scheme 7: Oxidation of aminocyclopropanes 20a–c.
Scheme 8: Synthesis of aminodioxolanes 24.
Figure 3: Trifluoromethyl-containing dioxolane 25.
Scheme 9: Synthesis of 1,2-dioxolanes 27a–e by the oxidation of cyclopropanes 26a–e.
Scheme 10: Photoinduced oxidation of methylenecyclopropanes 28.
Scheme 11: Irradiation-mediated oxidation.
Scheme 12: Application of diazene 34 for dioxolane synthesis.
Scheme 13: Mn(OAc)3-catalyzed cooxidation of arylacetylenes 37a–h and acetylacetone with atmospheric oxygen.
Scheme 14: Peroxidation of (2-vinylcyclopropyl)benzene (40).
Scheme 15: Peroxidation of 1,4-dienes 43a,b.
Scheme 16: Peroxidation of 1,5-dienes 46.
Scheme 17: Peroxidation of oxetanes 53a,b.
Scheme 18: Peroxidation of 1,6-diene 56.
Scheme 19: Synthesis of 3-alkoxy-1,2-dioxolanes 62a,b.
Scheme 20: Synthesis of spiro-bis(1,2-dioxolane) 66.
Scheme 21: Synthesis of dispiro-1,2-dioxolanes 68, 70, 71.
Scheme 22: Synthesis of spirohydroperoxydioxolanes 75a,b.
Scheme 23: Synthesis of spirohydroperoxydioxolane 77 and dihydroperoxydioxolane 79.
Scheme 24: Ozonolysis of azepino[4,5-b]indole 80.
Scheme 25: SnCl4-mediated fragmentation of ozonides 84a–l in the presence of allyltrimethylsilane.
Scheme 26: SnCl4-mediated fragmentation of bicyclic ozonide 84m in the presence of allyltrimethylsilane.
Scheme 27: MCl4-mediated fragmentation of alkoxyhydroperoxides 96 in the presence of allyltrimethylsilane.
Scheme 28: SnCl4-catalyzed reaction of monotriethylsilylperoxyacetal 108 with alkene 109.
Scheme 29: SnCl4-catalyzed reaction of triethylsilylperoxyacetals 111 with alkenes.
Scheme 30: Desilylation of tert-butyldimethylsilylperoxy ketones 131a,b followed by cyclization.
Scheme 31: Deprotection of peroxide 133 followed by cyclization.
Scheme 32: Asymmetric peroxidation of methyl vinyl ketones 137a–e.
Scheme 33: Et2NH-catalyzed intramolecular cyclization.
Scheme 34: Synthesis of oxodioxolanes 143a–j.
Scheme 35: Haloperoxidation accompanied by intramolecular ring closure.
Scheme 36: Oxidation of triterpenes 149a–d with Na2Cr2O7/N-hydroxysuccinimide.
Scheme 37: Curtius and Wolff rearrangements to form 1,2-dioxolane ring-retaining products.
Scheme 38: Oxidative desilylation of peroxide 124.
Scheme 39: Synthesis of dioxolane 158, a compound containing the aminoquinoline antimalarial pharmacophore.
Scheme 40: Diastereomers of plakinic acid A, 162a and 162b.
Scheme 41: Ozonolysis of alkenes.
Scheme 42: Cross-ozonolysis of alkenes 166 with carbonyl compounds.
Scheme 43: Ozonolysis of the bicyclic cyclohexenone 168.
Scheme 44: Cross-ozonolysis of enol ethers 172a,b with cyclohexanone.
Scheme 45: Griesbaum co-ozonolysis.
Scheme 46: Reactions of aryloxiranes 177a,b with oxygen.
Scheme 47: Intramolecular formation of 1,2,4-trioxolane 180.
Scheme 48: Formation of 1,2,4-trioxolane 180 by the reaction of 1,5-ketoacetal 181 with H2O2.
Scheme 49: 1,2,4-Trioxolane 186 with tetrazole fragment.
Scheme 50: 1,2,4-Trioxolane 188 with a pyridine fragment.
Scheme 51: 1,2,4-Trioxolane 189 with pyrimidine fragment.
Scheme 52: Synthesis of aminoquinoline-containing 1,2,4-trioxalane 191.
Scheme 53: Synthesis of arterolane.
Scheme 54: Oxidation of diarylheptadienes 197a–c with singlet oxygen.
Scheme 55: Synthesis of hexacyclinol peroxide 200.
Scheme 56: Oxidation of enone 201 and enenitrile 203 with singlet oxygen.
Scheme 57: Synthesis of 1,2-dioxanes 207 by oxidative coupling of carbonyl compounds 206 and alkenes 205.
Scheme 58: 1,2-Dioxanes 209 synthesis by co-oxidation of 1,5-dienes 208 and thiols.
Scheme 59: Synthesis of bicyclic 1,2-dioxanes 212 with aryl substituents.
Scheme 60: Isayama–Mukaiyama peroxysilylation of 1,5-dienes 213 followed by desilylation under acidic conditio...
Scheme 61: Synthesis of bicycle 218 with an 1,2-dioxane ring.
Scheme 62: Intramolecular cyclization with an oxirane-ring opening.
Scheme 63: Inramolecular cyclization with the oxetane-ring opening.
Scheme 64: Intramolecular cyclization with the attack on a keto group.
Scheme 65: Peroxidation of the carbonyl group in unsaturated ketones 228 followed by cyclization of hydroperox...
Scheme 66: CsOH and Et2NH-catalyzed cyclization.
Scheme 67: Preparation of peroxyplakoric acid methyl ethers A and D.
Scheme 68: Hg(OAc)2 in 1,2-dioxane synthesis.
Scheme 69: Reaction of 1,4-diketones 242 with hydrogen peroxide.
Scheme 70: Inramolecular cyclization with oxetane-ring opening.
Scheme 71: Inramolecular cyclization with MsO fragment substitution.
Scheme 72: Synthesis of 1,2-dioxane 255a, a structurally similar compound to natural peroxyplakoric acids.
Scheme 73: Synthesis of 1,2-dioxanes based on the intramolecular cyclization of hydroperoxides containing C=C ...
Scheme 74: Use of BCIH in the intramolecular cyclization.
Scheme 75: Palladium-catalyzed cyclization of δ-unsaturated hydroperoxides 271a–e.
Scheme 76: Intramolecular cyclization of unsaturated peroxyacetals 273a–d.
Scheme 77: Allyltrimethylsilane in the synthesis of 1,2-dioxanes 276a–d.
Scheme 78: Intramolecular cyclization using the electrophilic center of the peroxycarbenium ion 279.
Scheme 79: Synthesis of bicyclic 1,2-dioxanes.
Scheme 80: Preparation of 1,2-dioxane 286.
Scheme 81: Di(tert-butyl)peroxalate-initiated radical cyclization of unsaturated hydroperoxide 287.
Scheme 82: Oxidation of 1,4-betaines 291a–d.
Scheme 83: Synthesis of aminoquinoline-containing 1,2-dioxane 294.
Scheme 84: Synthesis of the sulfonyl-containing 1,2-dioxane.
Scheme 85: Synthesis of the amido-containing 1,2-dioxane 301.
Scheme 86: Reaction of singlet oxygen with the 1,3-diene system 302.
Scheme 87: Synthesis of (+)-premnalane А and 8-epi-premnalane A.
Scheme 88: Synthesis of the diazo group containing 1,2-dioxenes 309a–e.
Figure 4: Plakortolide Е.
Scheme 89: Synthesis of 6-epiplakortolide Е.
Scheme 90: Application of Bu3SnH for the preparation of tetrahydrofuran-containing bicyclic peroxides 318a,b.
Scheme 91: Application of Bu3SnH for the preparation of lactone-containing bicyclic peroxides 320a–f.
Scheme 92: Dihydroxylation of the double bond in the 1,2-dioxene ring 321 with OsO4.
Scheme 93: Epoxidation of 1,2-dioxenes 324.
Scheme 94: Cyclopropanation of the double bond in endoperoxides 327.
Scheme 95: Preparation of pyridazine-containing bicyclic endoperoxides 334a–c.
Scheme 96: Synthesis of 1,2,4-trioxanes 337 by the hydroperoxidation of unsaturated alcohols 335 with 1O2 and ...
Scheme 97: Synthesis of sulfur-containing 1,2,4-trioxanes 339.
Scheme 98: BF3·Et2O-catalyzed synthesis of the 1,2,4-trioxanes 342a–g.
Scheme 99: Photooxidation of enol ethers or vinyl sulfides 343.
Scheme 100: Synthesis of tricyclic peroxide 346.
Scheme 101: Reaction of endoperoxides 348a,b derived from cyclohexadienes 347a,b with 1,4-cyclohexanedione.
Scheme 102: [4 + 2]-Cycloaddition of singlet oxygen to 2Н-pyrans 350.
Scheme 103: Synthesis of 1,2,4-trioxanes 354 using peroxysilylation stage.
Scheme 104: Epoxide-ring opening in 355 with H2O2 followed by the condensation of hydroxy hydroperoxides 356 wi...
Scheme 105: Peroxidation of unsaturated ketones 358 with the H2O2/CF3COOH/H2SO4 system.
Scheme 106: Synthesis of 1,2,4-trioxanes 362 through Et2NH-catalyzed intramolecular cyclization.
Scheme 107: Reduction of the double bond in tricyclic peroxides 363.
Scheme 108: Horner–Wadsworth–Emmons reaction in the presence of peroxide group.
Scheme 109: Reduction of ester group by LiBH4 in the presence of 1,2,4-trioxane moiety.
Scheme 110: Reductive amination of keto-containing 1,2,4-trioxane 370.
Scheme 111: Reductive amination of keto-containing 1,2,4-trioxane and a Fe-containing moiety.
Scheme 112: Acid-catalyzed reactions of Н2О2 with ketones and aldehydes 374.
Scheme 113: Cyclocondensation of carbonyl compounds 376a–d using Me3SiOOSiMe3/CF3SO3SiMe3.
Scheme 114: Peroxidation of 4-methylcyclohexanone (378).
Scheme 115: Synthesis of symmetrical tetraoxanes 382a,b from aldehydes 381a,b.
Scheme 116: Synthesis of unsymmetrical tetraoxanes using of MeReO3.
Scheme 117: Synthesis of symmetrical tetraoxanes using of MeReO3.
Scheme 118: Synthesis of symmetrical tetraoxanes using of MeReO3.
Scheme 119: MeReO3 in the synthesis of symmetrical tetraoxanes with the use of aldehydes.
Scheme 120: Preparation of unsymmmetrical 1,2,4,5-tetraoxanes with high antimalarial activity.
Scheme 121: Re2O7-Catalyzed synthesis of tetraoxanes 398.
Scheme 122: H2SO4-Catalyzed synthesis of steroidal tetraoxanes 401.
Scheme 123: HBF4-Catalyzed condensation of bishydroperoxide 402 with 1,4-cyclohexanedione.
Scheme 124: BF3·Et2O-Catalyzed reaction of gem-bishydroperoxides 404 with enol ethers 405 and acetals 406.
Scheme 125: HBF4-Catalyzed cyclocondensation of bishydroperoxide 410 with ketones.
Scheme 126: Synthesis of symmetrical and unsymmetrical tetraoxanes 413 from benzaldehydes 412.
Scheme 127: Synthesis of bridged 1,2,4,5-tetraoxanes 415a–l from β-diketones 414a–l and H2O2.
Scheme 128: Dimerization of zwitterions 417.
Scheme 129: Ozonolysis of verbenone 419.
Scheme 130: Ozonolysis of O-methyl oxime 424.
Scheme 131: Peroxidation of 1,1,1-trifluorododecan-2-one 426 with oxone.
Scheme 132: Intramolecular cyclization of dialdehyde 428 with H2O2.
Scheme 133: Tetraoxanes 433–435 as by-products in peroxidation of ketals 430–432.
Scheme 134: Transformation of triperoxide 436 in diperoxide 437.
Scheme 135: Preparation and structural modifications of tetraoxanes.
Scheme 136: Structural modifications of steroidal tetraoxanes.
Scheme 137: Synthesis of 1,2,4,5-tetraoxane 454 containing the fluorescent moiety.
Scheme 138: Synthesis of tetraoxane 458 (RKA182).