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Search for "sodium ethoxide" in Full Text gives 35 result(s) in Beilstein Journal of Organic Chemistry.
An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles
- Marcus Baumann and
- Ian R. Baxendale
Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265
- presence of sodium ethoxide delivers epoxide 1.87. The material is next subjected to hydrogenolysis using Pd/C in methanol with a 1 bar hydrogen pressure to reductively ring open the epoxide. Finally, the transformation of the alcohol to the mesylate 1.88 occurs under standard conditions. In order to
Graphical Abstract
Scheme 1: Scaled industrial processes for the synthesis of simple pyridines.
Scheme 2: Synthesis of nicotinic acid from 2-methyl-5-ethylpyridine (1.11).
Scheme 3: Synthesis of 3-picoline and nicotinic acid.
Scheme 4: Synthesis of 3-picoline from 2-methylglutarodinitrile 1.19.
Scheme 5: Picoline-based synthesis of clarinex (no yields reported).
Scheme 6: Mode of action of proton-pump inhibitors and structures of the API’s.
Scheme 7: Hantzsch-like route towards the pyridine rings in common proton pump inhibitors.
Figure 1: Structures of rosiglitazone (1.40) and pioglitazone (1.41).
Scheme 8: Synthesis of rosiglitazone.
Scheme 9: Syntheses of 2-pyridones.
Scheme 10: Synthesis and mechanism of 2-pyrone from malic acid.
Scheme 11: Polymer-assisted synthesis of rosiglitazone.
Scheme 12: Synthesis of pioglitazone.
Scheme 13: Meerwein arylation reaction towards pioglitazone.
Scheme 14: Route towards pioglitazone utilising tyrosine.
Scheme 15: Route towards pioglitazone via Darzens ester formation.
Scheme 16: Syntheses of the thiazolidinedione moiety.
Scheme 17: Synthesis of etoricoxib utilising Negishi and Stille cross-coupling reactions.
Scheme 18: Synthesis of etoricoxib via vinamidinium condensation.
Figure 2: Structures of nalidixic acid, levofloxacin and moxifloxacin.
Scheme 19: Synthesis of moxifloxacin.
Scheme 20: Synthesis of (S,S)-2,8-diazabicyclo[4.3.0]nonane 1.105.
Scheme 21: Synthesis of levofloxacin.
Scheme 22: Alternative approach to the levofloxacin core 1.125.
Figure 3: Structures of nifedipine, amlodipine and clevidipine.
Scheme 23: Mg3N2-mediated synthesis of nifedipine.
Scheme 24: Synthesis of rac-amlodipine as besylate salt.
Scheme 25: Aza Diels–Alder approach towards amlodipine.
Scheme 26: Routes towards clevidipine.
Figure 4: Examples of piperidine containing drugs.
Figure 5: Discovery of tiagabine based on early leads.
Scheme 27: Synthetic sequences to tiagabine.
Figure 6: Structures of solifenacin (2.57) and muscarine (2.58).
Scheme 28: Enantioselective synthesis of solifenacin.
Figure 7: Structures of DPP-4 inhibitors of the gliptin-type.
Scheme 29: Formation of inactive diketopiperazines from cis-rotameric precursors.
Figure 8: Co-crystal structure of carmegliptin bound in the human DPP-4 active site (PDB 3kwf).
Scheme 30: Improved route to carmegliptin.
Figure 9: Structures of lamivudine and zidovudine.
Scheme 31: Typical routes accessing uracil, thymine and cytosine.
Scheme 32: Coupling between pyrimidones and riboses via the Vorbrüggen nucleosidation.
Scheme 33: Synthesis of lamivudine.
Scheme 34: Synthesis of raltegravir.
Scheme 35: Mechanistic studies on the formation of 3.22.
Figure 10: Structures of selected pyrimidine containing drugs.
Scheme 36: General preparation of pyrimidines and dihydropyrimidones.
Scheme 37: Synthesis of imatinib.
Scheme 38: Flow synthesis of imatinib.
Scheme 39: Syntheses of erlotinib.
Scheme 40: Synthesis of erlotinib proceeding via Dimroth rearrangement.
Scheme 41: Synthesis of lapatinib.
Scheme 42: Synthesis of rosuvastatin.
Scheme 43: Alternative preparation of the key aldehyde towards rosuvastatin.
Figure 11: Structure comparison between nicotinic acetylcholine receptor agonists.
Scheme 44: Syntheses of varenicline and its key building block 4.5.
Scheme 45: Synthetic access to eszopiclone and brimonidine via quinoxaline intermediates.
Figure 12: Bortezomib bound in an active site of the yeast 20S proteasome ([114], pdb 2F16).
Scheme 46: Asymmetric synthesis of bortezomib.
Figure 13: Structures of some prominent piperazine containing drugs.
Figure 14: Structural comparison between the core of aplaviroc (4.35) and a type-1 β-turn (4.36).
Scheme 47: Examplary synthesis of an aplaviroc analogue via the Ugi-MCR.
Scheme 48: Syntheses of azelastine (5.1).
Figure 15: Structures of captopril, enalapril and cilazapril.
Scheme 49: Synthesis of cilazapril.
Figure 16: Structures of lamotrigine, ceftriaxone and azapropazone.
Scheme 50: Synthesis of lamotrigine.
Scheme 51: Alternative synthesis of lamotrigine (no yields reported).
Figure 17: Structural comparison between imiquimod and the related adenosine nucleoside.
Scheme 52: Conventional synthesis of imiquimod (no yields reported).
Scheme 53: Synthesis of imiquimod.
Scheme 54: Synthesis of imiquimod via tetrazole formation (not all yields reported).
Figure 18: Structures of various anti HIV-medications.
Scheme 55: Synthesis of abacavir.
Figure 19: Structures of diazepam compared to modern replacements.
Scheme 56: Synthesis of ocinaplon.
Scheme 57: Access to zaleplon and indiplon.
Scheme 58: Different routes towards the required N-methylpyrazole 6.65 of sildenafil.
Scheme 59: Polymer-supported reagents in the synthesis of key aminopyrazole 6.72.
Scheme 60: Early synthetic route to sildenafil.
Scheme 61: Convergent preparations of sildenafil.
Figure 20: Comparison of the structures of sildenafil, tadalafil and vardenafil.
Scheme 62: Short route to imidazotriazinones.
Scheme 63: Alternative route towards vardenafils core imidazotriazinone (6.95).
Scheme 64: Bayer’s approach to the vardenafil core.
Scheme 65: Large scale synthesis of vardenafil.
Scheme 66: Mode of action of temozolomide (6.105) as methylating agent.
Scheme 67: Different routes to temozolomide.
Scheme 68: Safer route towards temozolomide.
Figure 21: Some unreported heterocyclic scaffolds in top market drugs.
The chemistry of bisallenes
- Henning Hopf and
- Georgios Markopoulos
Beilstein J. Org. Chem. 2012, 8, 1936–1998, doi:10.3762/bjoc.8.225
- chromatographic separation and purification [38]. Biallenyl 2 is also produced when 1,5-hexadiyne is treated with sodium ethoxide in ethanol at 65 °C for 24 h. But again this is not a practical preparative method since it results in the formation of too many other isomers of the substrate and 2 [39]. Alkylated
Graphical Abstract
Figure 1: Loschmidt’s structure proposal for benzene (1) (Scheme 181 from [3]) and the corresponding modern stru...
Figure 2: The first isolated bisallenes.
Figure 3: Carbon skeletons of selected bisallenes discussed in this review.
Scheme 1: The preparation of 1,2,4,5-hexatetraene (2).
Scheme 2: The preparation of a conjugated bisallene by the DMS-protocol.
Scheme 3: Preparation of the 3-deuterio- and 3,4-dideuterio derivatives of 24.
Scheme 4: A versatile method to prepare alkylated conjugated bisallenes and other allenes.
Scheme 5: A preparation of 3,4-dimethyl-1,2,4,5-hexatetraene (38).
Scheme 6: A (C6 + 0)-approach to 1,2,4,5-hexatetraene (2).
Scheme 7: The preparation of a fully alkylated bisallenes from a 2,4-hexadiyne-1,6-diol diacetate.
Scheme 8: The preparation of the first phenyl-substituted conjugated bisallenes 3 and 4.
Scheme 9: Selective hydrogenation of [5]cumulenes to conjugated bisallenes: another (C6 + 0)-route.
Scheme 10: Aryl-substituted conjugated bisallenes by a (C3 + C3)-approach.
Scheme 11: Hexaphenyl-1,2,4,5-hexatetraene (59) by a (C3 + C3)-approach.
Scheme 12: An allenation route to conjugated bisallenes.
Scheme 13: The preparation of 3,4-difunctionalized conjugated bisallenes.
Scheme 14: Problems during the preparation of sulfur-substituted conjugated bisallenes.
Scheme 15: The preparation of 3,4-dibromo bisallenes.
Scheme 16: Generation of allenolates by an oxy-Cope rearrangement.
Scheme 17: A linear trimerization of alkynes to conjugated bisallenes: a (C2 + C2 + C2)-protocol.
Scheme 18: Preparation of a TMS-substituted conjugated bisallene by a C3-dimerization route.
Scheme 19: A bis(trimethylsilyl)bisallene by a C3-coupling protocol.
Scheme 20: The rearrangement of highly substituted benzene derivatives into their conjugated bisallenic isomer...
Scheme 21: From fully substituted benzene derivatives to fully substituted bisallenes.
Scheme 22: From a bicyclopropenyl to a conjugated bisallene derivative.
Scheme 23: The conversion of a bismethylenecyclobutene into a conjugated bisallene.
Scheme 24: The preparation of monofunctionalized bisallenes.
Scheme 25: Preparation of bisallene diols and their cyclization to dihydrofurans.
Scheme 26: A 3,4-difunctionalized conjugated bisallene by a C3-coupling process.
Scheme 27: Preparation of a bisallenic diketone by a coupling reaction.
Scheme 28: Sulfur and selenium-substituted bisallenes by a [2.3]sigmatropic rearrangement.
Scheme 29: The biallenylation of azetidinones.
Scheme 30: The preparation of a fully ferrocenylated conjugated bisallene.
Scheme 31: The first isomerization of a 1,5-hexadiyne to a 1,2,4,5-hexatetraene.
Scheme 32: The preparation of alkynyl-substituted bisallenes by a C3-dimerization protocol.
Scheme 33: Preparation of another completely ferrocenylated bisallene.
Scheme 34: The cyclization of 1,5-hexadiyne (129) to 3,4-bismethylenecyclobutene (130) via 1,2,4,5-hexatetraen...
Scheme 35: Stereochemistry of the thermal cyclization of bisallenes to bismethylenecyclobutenes.
Scheme 36: Bisallene→bismethylenecyclobutene ring closures in the solid state.
Scheme 37: A bisallene cyclization/dimerization reaction.
Scheme 38: A selection of Diels–Alder additions of 1,2,4,5-hexatetraene with various double-bond dienophiles.
Scheme 39: The stereochemistry of the [2 + 4] cycloaddition to conjugated bisallenes.
Scheme 40: Preparation of azetidinone derivatives from conjugated bisallenes.
Scheme 41: Cycloaddition of heterodienophiles to a conjugated bisallene.
Scheme 42: Addition of triple-bond dienophiles to conjugated bisallenes.
Scheme 43: Sulfur dioxide addition to conjugated bisallenes.
Scheme 44: The addition of a germylene to a conjugated bisallene.
Scheme 45: Trapping of conjugated bisallenes with phosphinidenes.
Scheme 46: The cyclopropanantion of 1,2,4,5-hexatetraene (2).
Scheme 47: Photochemical reactions involving conjugated bisallenes.
Scheme 48: Base-catalyzed isomerizations of conjugated bisallenes.
Scheme 49: Ionic additions to a conjugated bisallene.
Scheme 50: Oxidation reactions of a conjugated bisallene.
Scheme 51: The mechanism of oxidation of the bisallene 24.
Scheme 52: CuCl-catalyzed cyclization of 1,2,4,5-hexatetraene (2).
Scheme 53: The conversion of conjugated bisallenes into cyclopentenones.
Scheme 54: Oligomerization of a conjugated bisallene by nickel catalysts.
Scheme 55: Generation of 1,2,5,6-heptatetraene (229) as a reaction intermediate.
Scheme 56: The preparation of a stable derivative of 1,2,5,6-heptatetraene.
Scheme 57: A bisallene with a carbonyl group as a spacer element.
Scheme 58: The first preparation of 1,2,6,7-octatetraene (242).
Scheme 59: Preparation of 1,2,6,7-octatetraenes by (C4 + C4)-coupling of enynes.
Scheme 60: Preparation of 1,2,6,7-octatetraenes by (C4 + C4)-coupling of homoallenyl bromides.
Scheme 61: Preparation of 1,2,6,7-octatetraenes by alkylation of propargylic substrates.
Scheme 62: Preparation of two highly functionalized 1,2,6,7-octatetraenes.
Scheme 63: Preparation of several higher α,ω-bisallenes.
Scheme 64: Preparation of different alkyl derivatives of α,ω-bisallenes.
Scheme 65: The preparation of functionalized 1,2,7,8-nonatetraene derivatives.
Scheme 66: Preparation of functionalized α,ω-bisallenes.
Scheme 67: The preparation of an α,ω-bisallene by direct homologation of an α,ω-bisalkyne.
Scheme 68: The gas-phase pyrolysis of 4,4-dimethyl-1,2,5,6-heptatetraene (237).
Scheme 69: Gas-phase pyrolysis of 1,2,6,7-octatetraene (242).
Scheme 70: The cyclopropanation of 1,2,6,7-octatetraene (242).
Scheme 71: Intramolecular cyclization of 1,2,6,7-octatetraene derivatives.
Scheme 72: The gas-phase pyrolysis of 1,2,7,8-nonatetraene (265) and 1,2,8,9-decatetraene (266).
Scheme 73: Rh-catalyzed cyclization of a functionalized 1,2,7,8-nonatetraene.
Scheme 74: A triple cyclization involving two different allenic substrates.
Scheme 75: Bicyclization of keto derivatives of 1,2,7,8-nonatetraene.
Scheme 76: The preparation of complex organic compounds from functionalized bisallenes.
Scheme 77: Cycloisomerization of an α,ω-bisallene containing a C9 tether.
Scheme 78: Organoborane polymers from α,ω-bisallenes.
Scheme 79: Preparation of trans- (337) and cis-1,2,4,6,7-octapentaene (341).
Scheme 80: The preparation of 4-methylene-1,2,5,6-heptatetraene (349).
Scheme 81: The preparation of acetylenic bisallenes.
Scheme 82: The preparation of derivatives of hydrocarbon 351.
Scheme 83: The construction of macrocyclic alleno-acetylenes.
Scheme 84: Preparation and reactions of 4,5-bismethylene-1,2,6,7-octatetraene (365).
Scheme 85: Preparation of 1,2-bis(propadienyl)benzene (370).
Scheme 86: The preparation of 1,4-bis(propadienyl)benzene (376).
Scheme 87: The preparation of aromatic and heteroaromatic bisallenes by metal-mediated coupling reactions.
Scheme 88: Double cyclization of an aromatic bisallene.
Scheme 89: Preparation of an allenic [15]paracyclophane by a ring-closing metathesis reaction of an aromatic α...
Scheme 90: Preparation of a macrocyclic ring system containing 1,4-bis(propadienyl)benzene units.
Scheme 91: Preparation of copolymers from 1,4-bis(propadienyl)benzene (376).
Scheme 92: A boration/copolymerization sequence of an aromatic bisallene and an aromatic bisacetylene.
Scheme 93: Formation of a layered aromatic bisallene.
Figure 4: The first members of the semicyclic bisallene series.
Scheme 94: Preparation of the first bis(vinylidene)cyclobutane derivative.
Scheme 95: Dimerization of strain-activated cumulenes to bis(vinylidene)cyclobutanes.
Scheme 96: Photodimerization of two fully substituted butatrienes in the solid state.
Scheme 97: Preparation of the two parent bis(vinylidene)cyclobutanes.
Scheme 98: The preparation of 1,3-bis(vinylidene)cyclopentane and its thermal isomerization.
Scheme 99: The preparation of the isomeric bis(vinylidene)cyclohexanes.
Scheme 100: Bi- and tricyclic conjugated bisallenes.
Scheme 101: A selection of polycyclic bisallenes.
Scheme 102: The first endocyclic bisallenes.
Figure 5: The stereochemistry of 1,2,6,7-cyclodecatetraene.
Scheme 103: The preparation of several endocyclic bisallenes.
Scheme 104: Synthesis of diastereomeric derivatives of 1,2,6,7-cyclodecatetraene.
Scheme 105: Preparation of a derivative of 1,2,8,9-cyclotetradecatetraene.
Scheme 106: The preparation of keto derivatives of cyclic bisallenes.
Scheme 107: The preparation of cyclic biscumulenic ring systems.
Scheme 108: Cyclic bisallenes in natural- and non-natural-product chemistry.
Scheme 109: The preparation of iron carbonyl complexes from cyclic bisallenes.
Figure 6: A selection of unknown exocyclic bisallenes that should have interesting chemical properties.
Scheme 110: The thermal isomerization of 1,2-diethynylcyclopropanes and -cyclobutanes.
Scheme 111: Intermediate generation of a cyclooctapentaene.
Scheme 112: Attempted preparation of a cyclodecahexaene.
Scheme 113: The thermal isomerization of 1,5,9-cyclododecatriyne (511) into [6]radialene (514).
Scheme 114: An isomerization involving a diketone derived from a conjugated bisallene.
Scheme 115: Typical reaction modes of heteroorganic bisallenes.
Scheme 116: Generation and thermal behavior of acyclic hetero-organic bisallenes.
Scheme 117: Generation of bis(propadienyl)thioether.
Scheme 118: The preparation of a bisallenic sulfone and its thermal isomerization.
Scheme 119: Bromination of the bisallenic sulfone 535.
Scheme 120: Metalation/hydrolysis of the bisallenic sulfone 535.
Scheme 121: Aromatic compounds from hetero bisallenes.
Scheme 122: Isomerization/cyclization of bispropargylic ethers.
Scheme 123: The preparation of novel aromatic systems by base-catalyzed isomerization of bispropargyl ethers.
Scheme 124: The isomerization of bisacetylenic thioethers to bicyclic thiophenes.
Scheme 125: Aromatization of macrocyclic bispropargylic sulfides.
Scheme 126: Preparation of ansa-compounds from macrocyclic bispropargyl thioethers.
Scheme 127: Alternate route for cyclization of a heterorganic bisallene.
Scheme 128: Multiple isomerization/cyclization of “double” bispropargylic thioethers.
Scheme 129: Preparation of a bisallenyl disulfide and its subsequent bicyclization.
Scheme 130: Thermal cyclization of a bisallenyl thiosulfonate.
Scheme 131: Some reactions of heteroorganic bisallenes with two sulfur atoms.
Scheme 132: Further methods for the preparation of heteroorganic bisallenes.
Scheme 133: Cyclization reactions of heteroorganic bisallenes.
Scheme 134: Thermal cycloadditions of bisallenic tertiary amines.
Scheme 135: Cyclization of a bisallenic tertiary amine in the presence of a transition-metal catalyst.
Scheme 136: A Pauson–Khand reaction of a bisallenic ether.
Scheme 137: Formation of a 2:1adduct from two allenic substrates.
Scheme 138: A ring-forming silastannylation of a bisallenic tertiary amine.
Scheme 139: A three-component cyclization involving a heterorganic bisallene.
Scheme 140: Atom-economic construction of a complex organic framework from a heterorganic α,ω-bisallene.
Influence of cyclodextrin on the solubility of a classically prepared 2-vinylcyclopropane macromonomer in aqueous solution
- Helmut Ritter,
- Jia Cheng and
- Monir Tabatabai
Beilstein J. Org. Chem. 2012, 8, 1528–1535, doi:10.3762/bjoc.8.173
- (4) was synthesized following a procedure described in [32]. Diethyl 2-vinyl-1,1-cyclopropanedicarboxylate could be obtained according to [33] from sodium ethoxide, diethyl malonate and trans-1,4-dichloro-2-butene in ethanol (Scheme 2). The desired macromonomer 5 was prepared in two steps according
Graphical Abstract
Scheme 1: Mechanism of free radical ring-opening polymerization of 2-VCPs (In: initiator) [29-31].
Scheme 2: Synthesis of diethyl 2-vinyl-1,1-cyclopropanedicarboxylate [33].
Scheme 3: Two-step synthesis of the macromonomer 5 (In: Initiator, TEA: triethylamine).
Figure 1: MALDI-TOF MS of amino-terminated poly(NiPAAm) 3.
Figure 2: Optical transmittance of aqueous solutions (c = 20 mg/mL) of 3, 6 und 8 during heating.
Figure 3: 2D ROESY NMR spectrum of a 5/Me2-β-CD deuterated water solution.
Figure 4: Temperature-dependent transparency measurements of aqueous solution of the supramolecular complex 7...
Scheme 4: Homo- and copolymerization of macromonomer 5.
Sexithiophenes as efficient luminescence quenchers of quantum dots
- Christopher R. Mason,
- Yang Li,
- Paul O’Brien,
- Neil J. Findlay and
- Peter J. Skabara
Beilstein J. Org. Chem. 2011, 7, 1722–1731, doi:10.3762/bjoc.7.202
- = 4.4, 2H); MS (EI) m/z: 338 (M+, 51%), 310 (19%), 265 (19%); MS (CI) m/z: 356 (M + NH4+, 5%), 339 (M + H+, 100%). 5,7-Dithiophen-2-yl-2,3-dihydrothieno[3,4-b][1,4]dithiine (5) [30] To a solution of the terthiophene D (2.17 g, 6.4 mmol) in dry tetrahydrofuran (150 mL), was added sodium ethoxide (0.2 M
Graphical Abstract
Figure 1: Dimethylaminophenylene end-capped sexithiophenes 1a and 1b, and dialkyl end-capped sexithiophenes 2a...
Scheme 1: The synthesis of functionalised oligothiophenes 1a,b and 2a,b. Reagents and conditions: a) NBS, CH3...
Figure 2: Solid-state voltammograms of 1b and 2b, as spin-coated films on ITO glass, versus Ag/AgCl reference...
Figure 3: Absorption spectra in solution (dichloromethane) and solid state.
Figure 4: UV–visible spectroelectrochemical measurements of 1b (left) and 2b (right) drop-cast onto ITO glass....
Figure 5: Absorption spectra for 1b and 2b, together with the absorption and emission profiles for the CdSe(Z...
Figure 6: The absorption spectra of increasing sexithiophene concentration with HDA capped CdSe(ZnS) quantum ...
Figure 7: Photoluminescence quenching experiments; the effect of increasing sexithiophene concentration with ...
Approaches towards the synthesis of 5-aminopyrazoles
- Ranjana Aggarwal,
- Vinod Kumar,
- Rajiv Kumar and
- Shiv P. Singh
Beilstein J. Org. Chem. 2011, 7, 179–197, doi:10.3762/bjoc.7.25
- intermediacy of the acyclic cyano derivative 127 (Scheme 34) [76]. Hydrazonoyl chlorides 129 on treatment with benzothiazole-2-acetonitrile in ethanolic sodium ethoxide solution at room temperature afforded intermediate hydrazones 130 which on cyclization gave products identified as 3-substituted 5-amino-1
- sodium ethoxide (Scheme 47). Ioannidou and Koutentis [91] investigated the conversion of isothiazoles into pyrazoles on treatment with hydrazine. The influence of various C-3, C-4 and C-5 isothiazole substituents and some limitations of this ring transformation were investigated. When a good nucleofugal
Graphical Abstract
Figure 1: Pharmacologically active 5-aminopyrazoles.
Scheme 1: General equation for the condensation of β-ketonitriles with hydrazines.
Scheme 2: Reaction of hydrazinoheterocycles with α-phenyl-β-cyanoketones (4).
Scheme 3: Condensation of cyanoacetaldehyde (7) with hydrazines.
Scheme 4: Synthesis of 5-aminopyrazoles and their sulfonamide derivatives.
Scheme 5: Synthesis of 5-aminopyrazoles, containing a cyclohexylmethyl- or phenylmethyl- sulfonamido group at...
Scheme 6: Regioselective synthesis of 3-amino-2-alkyl (or aryl) thieno[3,4-c]pyrazoles 19.
Scheme 7: Solid supported synthesis of 5-aminopyrazoles.
Scheme 8: Synthesis of 5-aminopyrazoles from resin supported enamine nitrile 25 as the starting material.
Scheme 9: Two-step “catch and release” solid-phase synthesis of 3,4,5-trisubstituted pyrazoles.
Scheme 10: Synthesis of pyrazolo[5,1-d][1,2,3,5]tetrazine-4(3H)-ones.
Scheme 11: Synthesis of the 5,5-ring system, imidazo[1,2-b]pyrazol-2-ones.
Scheme 12: Synthesis of 5-amino-3-(pyrrol-2-yl)pyrazole-4-carbonitrile.
Scheme 13: Synthesis of N-(1,3-diaryl-1H-pyrazol-5-yl)benzamide.
Scheme 14: Synthesis of 3,7-bis(arylazo)-6-methyl-2-phenyl-1H-imidazo[1,2-b]pyrazoles.
Scheme 15: Synthesis of 3,5-diaminopyrazole.
Scheme 16: Synthesis of 5-amino-4-cyanopyrazole and 5-amino-3-hydrazinopyrazole.
Scheme 17: Synthesis of 3,5-diaminopyrazoles with substituted malononitriles.
Scheme 18: Synthesis of 3,5-diamino-4-oximinopyrazole.
Scheme 19: Synthesis of 4-arylazo-3,5-diaminopyrazoles.
Scheme 20: Synthesis of 3- or 5-amino-4-cyanopyrazoles.
Scheme 21: Synthesis of triazenopyrazoles.
Scheme 22: Synthesis of 5(3)-aminopyrazoles.
Scheme 23: Synthesis of 3-substituted 5-amino-4-cyanopyrazoles.
Scheme 24: Synthesis of 2-{[(1-acetyl-4-cyano-1H-pyrazol-5-yl)amino]methylene}malononitrile.
Scheme 25: Synthesis of 5-aminopyrazole carbodithioates and 5-amino-3-arylamino-1-phenylpyrazole-4-carboxamide...
Scheme 26: Synthesis of 5-amino-4-cyanopyrazoles.
Scheme 27: Synthesis of thiazolylpyrazoles.
Scheme 28: Synthesis of 5-amino-1-heteroaryl-3-methyl/aryl-4-cyanopyrazoles.
Scheme 29: Synthesis of 5-amino-3-methylpyrazole-4-carboxamide.
Scheme 30: Synthesis of 4-acylamino-3(5)-amino-5(3)-arylsulfanylpyrazoles.
Scheme 31: Synthesis of 5-amino-1-aryl-4-diethoxyphosphoryl-3-halomethylpyrazoles.
Scheme 32: Synthesis of substituted 5-amino-3-trifluoromethylpyrazoles 114 and 118.
Scheme 33: Solid-support synthesis of 5-N-alkylamino and 5-N-arylaminopyrazoles.
Scheme 34: Synthesis of 5-amino-1-cyanoacetyl-3-phenyl-1H-pyrazole.
Scheme 35: Synthesis of 3-substituted 5-amino-1-aryl-4-(benzothiazol-2-yl)pyrazoles.
Scheme 36: Synthesis of 5-amino-4-carbethoxy-3-methyl-1-(4-sulfamoylphenyl)pyrazole.
Scheme 37: Synthesis of inhibitors of hsp27-phosphorylation and TNFa-release.
Scheme 38: Synthesis of the diglycylpyrazole 142.
Scheme 39: Synthesis of 5-amino-1-aryl-4-benzoylpyrazole derivatives.
Scheme 40: Synthesis of 4-benzoyl-3,5-diamino-1-(2-cyanoethyl)pyrazole.
Scheme 41: Synthesis of the 5-aminopyrazole derivative 150.
Scheme 42: Synthesis of 3,5-diaminopyrazoles 153.
Scheme 43: Synthesis of 5-aminopyrazoles derivatives 155 via lithiated intermediates.
Scheme 44: Synthesis of 5-amino-4-(1,2,4-oxadiazol-5-yl)-pyrazoles 157.
Scheme 45: Synthesis of a 5-aminopyrazole with anticonvulsant activity.
Scheme 46: Synthesis of tetrasubstituted 5-aminopyrazole derivatives.
Scheme 47: Synthesis of substituted 5-aminopyrazoles from hydrazonoyl halides.
Scheme 48: Synthesis of 3-amino-5-phenylpyrazoles from isothiazoles.
Scheme 49: Synthesis of 5-aminopyrazoles via ring transformation.
Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives
- Filipe Vilela,
- Peter J. Skabara,
- Christopher R. Mason,
- Thomas D. J. Westgate,
- Asun Luquin,
- Simon J. Coles and
- Michael B. Hursthouse
Beilstein J. Org. Chem. 2010, 6, 1002–1014, doi:10.3762/bjoc.6.113
- solution of 8-(2-thienyl)thieno[2,3-f][1,3]benzodithiole-2-thione 3 (0.092 g, 2.85 × 10−4 mol) in dry THF (10 ml) under a nitrogen atmosphere, was added sodium ethoxide (0.1 M aqueous solution, 2.85 ml, 2.85 × 10−4 mol) and the mixture heated under reflux for 1 h. Tetrabutylammonium bromide (0.097 g, 3.01
Graphical Abstract
Figure 1: Chemical structures of compounds 1–3.
Scheme 1: Acid-catalysed behaviour of 4,5-bis(2-arylhydroxymethyl)-1,3-dithiole-2-thiones 2.
Scheme 2: The proposed mechanism for the formation of 3.
Scheme 3: The proposed mechanism for the decomposition of 13 in the presence of perchloric acid.
Figure 2: Generalised structure of diol 17.
Scheme 4: Reagents and conditions: (i) LDA (1 equiv), 2,4-dimethoxybenzaldehyde (1 equiv), then repeat, −78 °...
Scheme 5: Reagents and conditions: (i) ethylenediamine, AcOH, MeOH; (ii) P(OEt)3, 120 °C, 3 h.
Figure 3: Molecular structure and numbering scheme of compound 22 with Hs omitted.
Scheme 6: Reagents and conditions: (i) P(OEt)3, reflux; (ii) Hg(OAc)2, CH2Cl2/AcOH; (iii) NaOEt, THF, reflux,...
Figure 4: Molecular structure of 28 with the tetrabutylammonium cation omitted.
Figure 5: Packing diagram of 28 identifying close intermolecular contacts.
Figure 6: UV–visible spectra of 3, 25, 27 and 28 in CH2Cl2 solution.
Figure 7: Cyclic voltammograms of compounds 3, 25, 27, and 28. Glassy carbon working electrode, using Pt wire...
Synthesis of 3-(quinolin-2-yl)- and 3,6-bis(quinolin-2-yl)-9H-carbazoles
- Yang Li and
- Wentao Gao
Beilstein J. Org. Chem. 2010, 6, 966–972, doi:10.3762/bjoc.6.108
- Yang Li Wentao Gao Institute of Superfine Chemicals, Bohai University, Jinzhou 121000, China 10.3762/bjoc.6.108 Abstract A simple and efficient synthesis of novel 3-(quinolin-2-yl)- and 3,6-bis(quinolin-2-yl)-9H-carbazoles, utilizing sodium ethoxide as a catalyst via a Friedländer condensation
- : acetylcarbazole; β-aminoaldehyde; β-aminoketone; Friedländer condensation; sodium ethoxide; Introduction Nitrogen-containing heterocycles are a very important group of organic compounds because of their wide application in medicine, agriculture, and technology. Among these, quinoline and carbazole derivatives
- quinolines under mild conditions catalysed by sodium ethoxide. In connection with our studies, we envisioned that the procedure could also be applied to the reaction of 3-acetyl-9-ethyl-9H-carbazole or 3,6-diacetyl-9-ethyl-9H-carbazole with 2-aminoaldehydes or 2-aminoketones, from which the quinolycarbazoles
9,10-Dioxa-1,2-diaza-anthracene derivatives from tetrafluoropyridazine
- Graham Pattison,
- Graham Sandford,
- Dmitrii S. Yufit,
- Judith A. K. Howard,
- John A. Christopher and
- David D. Miller
Beilstein J. Org. Chem. 2010, 6, No. 45, doi:10.3762/bjoc.6.45
- substitution ring annelation process, further extending the use of perfluoroheteroaromatic derivatives for the synthesis of unusual polyfunctional heterocyclic architectures. The tricyclic scaffold reacts with amines and sodium ethoxide providing a short series of functional 9,10-dioxa-1,2-diaza-anthracene
- publication CCDC-764716. Reaction of 3,4-difluoro-9,10-dioxa-1,2-diaza-anthracene (5) with sodium ethoxide 4-Ethoxy-3-fluoro-9,10-dioxa-1,2-diaza-anthracene (9c) Using the procedure described above, 3,4-difluoro-9,10-dioxa-1,2-diaza-anthracene (5) (0.10 g, 0.45 mmol), sodium ethoxide (0.06 g, 0.90 mmol) and
Graphical Abstract
Scheme 1: Synthesis of novel tricyclic heterocycles from pentafluoropyridine.
Scheme 2: Synthetic route to dioxa-diaza-anthracene derivatives.
Scheme 3: Reactions of tetrafluoropyridazine 3 with sodium phenoxide.
Scheme 4: Synthesis of dioxa-1,2-diaza-anthracene scaffold 5.
Scheme 5: Mechanism of formation of 5.
Scheme 6: Reactions of dioxa-1,2-diaza-anthracene scaffold 5 with nucleophiles.
Figure 1: Molecular structure of 4-allylamino-3-fluoro-9,10-dioxa-1,2-diaza-anthracene (9b).
An expedient and new synthesis of pyrrolo[1,2-b]pyridazine derivatives
- Rajeshwar Reddy Sagyam,
- Ravinder Buchikonda,
- Jaya Prakash Pitta,
- Himabindu Vurimidi,
- Pratap Reddy Padi and
- Mahesh Reddy Ghanta
Beilstein J. Org. Chem. 2009, 5, No. 66, doi:10.3762/bjoc.5.66
- condensation reactions, such as the condensation of oxazolo[3,2-b]pyridazinium perchlorates with malononitrile, ethyl cyanoacetate and ethyl malonate in the presence of sodium ethoxide [15]; the condensation of 1,4,7-triketones with hydrazine followed by dehydrogenation [16]; the condensation of cyanoacetic
Graphical Abstract
Figure 1: Unsubstituted pyrrolo[1,2-b]pyridazine.
Scheme 1: Reagents and conditions: i) p-TSA (0.5 equiv), toluene/cyclohexane (4:15), reflux, 15–18 h; ii) p-T...
Figure 2: Depiction with proprietary numbering of compound 6a.
Scheme 2: Plausible mechanistic pathway.
Scheme 3: Reagents and conditions: i) p-TSA (1.5 equiv), toluene/cyclohexane (1:1), reflux, 10.0 h.
Scheme 4: Reagents and conditions: i) p-TSA (2.0 equiv), toluene (30.0 volumes).
A facile synthesis and fungicidal activities of 2-(alkylamino)-5,6-dimethylthieno[2,3-d]pyrimidin- 4(3H)-ones
- Yang-Gen Hu,
- Ai-Hua Zheng,
- Xu-Zhi Ruan and
- Ming-Wu Ding
Beilstein J. Org. Chem. 2008, 4, No. 49, doi:10.3762/bjoc.4.49
- carbodiimides 4, which were allowed to react with secondary amines to provide guanidine intermediates 5. Even in refluxing toluene, compounds 5 did not cyclize. However, in the presence of a catalytic amount of sodium ethoxide, compounds 5 were converted easily to 2-(dialkylamino)-5,6-dimethylthieno[2,3-d
Graphical Abstract
Scheme 1: Preparation of iminophosphorane 3.
Scheme 2: Preparation of 2-(dialkylamino)-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-ones 6.
Scheme 3: Preparation of 2-alkylamino-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-ones 8.
