CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• subunits. Bryden and Boyle [29] presented a mild and facile one-pot synthesis of meso-substituted zinc(II) azido-porphyrin 39a–c in excellent yield by using a diazo-transfer reagent and utilized it for the preparation of 1,2,3-triazole-linked porphyrin conjugates 40a,b using copper(I)-catalyzed click

Synthesis and reactivity of azole-based iodazinium salts

• Thomas J. Kuczmera,
• Annalena Dietz,
• Andreas Boelke and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2023, 19, 317–324, doi:10.3762/bjoc.19.27

• imidazoiodaziniums, we show highly delicate post-oxidation functionalizations retaining the hypervalent iodine center. Keywords: building block; heterocycles; hypervalent compounds; iodonium salts; one-pot synthesis; Introduction The chemistry of hypervalent iodine compounds, in particular aryl-λ3-iodanes, is

An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies

• Tharun K. Kotammagari,
• Sweta Misra,
• Sayantan Paul,
• Sunita Kunte,
• Rajesh G. Gonnade,
• Manas K. Santra and
• Asish K. Bhattacharya

Beilstein J. Org. Chem. 2023, 19, 204–211, doi:10.3762/bjoc.19.19

• configuration of each enantiomer was determined by single-crystal X-ray analysis. In addition, a one-pot synthesis of (±)-incarviditone has been achieved from rac-rengyolone by using KHMDS as a base. We have also assessed the anticancer activity of all the synthesized compounds in breast cancer cells

Organophosphorus chemistry: from model to application

• György Keglevich

Beilstein J. Org. Chem. 2023, 19, 89–90, doi:10.3762/bjoc.19.8

• . elaborated a Lewis acid-catalyzed one-pot synthesis of phosphinates and phosphonates staring from pyridinecarboxaldehydes and diarylphosphine oxides [2]. This protocol is the analogy of the Pudovik reaction, followed by the phospha-Brook rearrangement applied mainly for the synthesis of phosphoric ester

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

• Elena R. Lopat’eva,
• Igor B. Krylov,
• Dmitry A. Lapshin and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

• biomimetic oxidation of benzyl alcohols was developed using o-naphthoquinone [129] (Scheme 28). The reaction shows regioselectivity toward benzylic alcohol oxidation. This process could be included in one-pot synthesis strategies. The key step of the reaction is a 1,5-hydrogen transfer (the suggested

One-pot synthesis of 2-arylated and 2-alkylated benzoxazoles and benzimidazoles based on triphenylbismuth dichloride-promoted desulfurization of thioamides

• Arisu Koyanagi,
• Yuki Murata,
• Shiori Hayakawa,
• Mio Matsumura and
• Shuji Yasuike

Beilstein J. Org. Chem. 2022, 18, 1479–1487, doi:10.3762/bjoc.18.155

Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions

• Michael Keppler,
• Sandra Moser,
• Henning J. Jessen,
• Christoph Held and
• Jennifer N. Andexer

Beilstein J. Org. Chem. 2022, 18, 1278–1288, doi:10.3762/bjoc.18.134

• an analytical scale, this reaction reached conversions of up to 94%, which agrees with the thermodynamic equilibrium for acetate kinase of at least 90%:10% ATP:ADP [26]. A comparable one-pot synthesis was recently published by the group of Li (Table 1) using two PPKs (PPK2-II and PPK2-I) with polyP

A versatile way for the synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with the NaBH₄/I₂ system

• Lin Chen,
• Xuan Zhou,
• Zhiyong Chen,
• Changxu Wang,
• Shunjie Wang and
• Hanbing Teng

Beilstein J. Org. Chem. 2022, 18, 1032–1039, doi:10.3762/bjoc.18.104

• Lin Chen Xuan Zhou Zhiyong Chen Changxu Wang Shunjie Wang Hanbing Teng School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, 122 Luoshi Road, Wuhan, 430070, China 10.3762/bjoc.18.104 Abstract An economical and versatile protocol for the one-pot synthesis of

• . In the whole process, no extra carbon was introduced. Conclusion In conclusion, we have developed an economical and versatile protocol for the one-pot synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with the NaBH4/I2 system. This work further extends the application of

Synthesis of novel alkynyl imidazopyridinyl selenides: copper-catalyzed tandem selenation of selenium with 2-arylimidazo[1,2-a]pyridines and terminal alkynes

• Mio Matsumura,
• Kaho Tsukada,
• Kiwa Sugimoto,
• Yuki Murata and
• Shuji Yasuike

Beilstein J. Org. Chem. 2022, 18, 863–871, doi:10.3762/bjoc.18.87

• their applications in the biological and pharmaceutical fields. The Cu-catalyzed tandem reaction for the synthesis of novel alkynyl imidazopyridinyl selenides is presented. A one-pot synthesis route afforded alkynyl imidazopyridinyl selenides in moderate to good yields. This was achieved by a two-step

Heteroleptic metallosupramolecular aggregates/complexation for supramolecular catalysis

• Prodip Howlader and
• Michael Schmittel

Beilstein J. Org. Chem. 2022, 18, 597–630, doi:10.3762/bjoc.18.62

• advantages of utilizing self-assembly to construct discrete nanocages with predetermined geometry and function is the use of a one-pot reaction employing complementary organic linkers with inorganic metal ions. Although the one-pot synthesis of homoleptic metallacages has been thoroughly investigated over

• solvents restricts their use in potential applications. In this aspect, coordination-driven discrete architectures provide a promising future due to their facile one-pot synthesis and high solubility in common solvents. Mukherjee and co-workers have developed supramolecular architectures containing

Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives

• Sayan Pramanik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 469–478, doi:10.3762/bjoc.18.49

• proves that two equivalents of 3-phenacylideneoxindole are required for reductive cyclodimerization. Conclusion In conclusion, we have successfully developed a simple and efficient methodology towards the one-pot synthesis of dispirocyclopentanebisoxindole derivatives through base-catalyzed reductive

Synthesis of 5-unsubstituted dihydropyrimidinone-4-carboxylates from deep eutectic mixtures

• Sangram Gore,
• Sundarababu Baskaran and
• Burkhard König

Beilstein J. Org. Chem. 2022, 18, 331–336, doi:10.3762/bjoc.18.37

• Sangram Gore Sundarababu Baskaran Burkhard Konig Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India Institut für Organische Chemie, Universität Regensburg, Universitätsstraße 31, D-93040 Regensburg, Germany 10.3762/bjoc.18.37 Abstract A facile one-pot synthesis

• -unsubstituted 3,4-dihydropyrimidinone-4-carboxylate derivatives by employing oxalacetic acid as a β-ketoester equivalent in the presence of TFA via a Biginelli reaction [23]. Lam and Fang reported the same synthesis under microwave conditions [24]. Very recently, Kambappa and co-workers reported a one-pot

• synthesis of 5-unsubstituted dihydropyrimidinone-4-carboxylate using gem-dibromomethylarene, oxalacetic acid, and urea [25]. Here the gem-dibromomethylarene moiety serves as an aldehyde equivalent. In addition, utilizing aromatic ketones as a β-ketoester equivalent, the synthesis of 5-unsubstituted DHPM

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

• Surendran Amrutha,
• Sankaran Radhika and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

• -substituted iodobenzenes catalyzed by in situ-generated α-Fe2O3 nanoparticles. One-pot synthesis of 2-arylbenzo[b]furans via tandem Sonogashira coupling–cyclization protocol. Suggested mechanism of the Fe(III) catalyzed coupling of o-iodophenol with acetylene derivatives. Fe3O4@SiO2/Schiff base/Fe(II

Recent advances and perspectives in ruthenium-catalyzed cyanation reactions

• Thaipparambil Aneeja,
• Cheriya Mukkolakkal Abdulla Afsina,
• Padinjare Veetil Saranya and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 37–52, doi:10.3762/bjoc.18.4

• strategy. Proposed mechanistic pathway for the cyanation of the aldimine intermediate. Strecker-type functionalization of N-aryl-substituted tetrahydroisoquinolines under flow conditions. One-pot synthesis of α-aminonitriles using RuCl3 as catalyst. Synthesis of alkyl nitriles using (Ru(TMHD)3) as the

Total synthesis of the O-antigen repeating unit of Providencia stuartii O49 serotype through linear and one-pot assemblies

• Tanmoy Halder and
• Somnath Yadav

Beilstein J. Org. Chem. 2021, 17, 2915–2921, doi:10.3762/bjoc.17.199

• involving the [1 + (1 + 1 = 2)] assembly, followed by a one-pot synthesis involving [1 + 1 + 1] strategy from the corresponding monosaccharides. The one-pot method provided a higher yield of the protected trisaccharide intermediate (73%) compared to the two step synthesis (66%). The protected trisaccharide

• was then deprotected and N-acetylated to finally afford the desired trisaccharide repeating unit as its α-p-methoxyphenyl glycoside. Keywords: capsular polysaccharide; carbohydrate vaccines; O-antigen; oligosaccharide synthesis; one-pot synthesis; Introduction O-antigens or O-specific

• acceptor. We also demonstrated a follow-up one-pot synthesis involving a [1 + 1 + 1] strategy using the corresponding appropriately protected monosaccharides, providing the opportunity for rapid access to the desired target molecule. Results and Discussion The retrosynthesis of the target trisaccharide 1

A two-phase bromination process using tetraalkylammonium hydroxide for the practical synthesis of α-bromolactones from lactones

• Yuki Yamamoto,
• Akihiro Tabuchi,
• Kazumi Hosono,
• Takanori Ochi,
• Kento Yamazaki,
• Shintaro Kodama,
• Akihiro Nomoto and
• Akiya Ogawa

Beilstein J. Org. Chem. 2021, 17, 2906–2914, doi:10.3762/bjoc.17.198

• layer was washed with H2O (10 mL × 2), dried by anhydrous Na2SO4, then filtered. The filtrate was concentrated under reduced pressure. Finally, the residue was purified by silica-gel column chromatography (AcOMe/isohexane) to give pure product 5. One-pot synthesis of a functional lactone 6 using PhS−Na

• 2a. Synthesis of α-functionalized lactones using the two-phase system. Synthesis of unsymmetrically functionalized sulfide 5 via the two-phase system-promoted intramolecular cyclization of 2b. Sequential nucleophilic substitution in the two-phase system. One-pot synthesis of 2-phenylthio-α

Recent advances in the syntheses of anthracene derivatives

• Giovanni S. Baviera and
• Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

• -workers reported a one-pot synthesis of substituted anthracenes 37 from o-tolualdehyde 34 and aryl iodides 35 via a palladium-catalyzed C–H arylation with a silver oxidant (Scheme 8) [42]. During optimization studies, the authors noted that steric and electronic effects strongly affected the cyclization

• reaction also included anthraquinones 173b and 173c, obtained in good yields (74–94%) [73]. In 2015, in a related approach, Lee et al. disclosed a direct one-pot synthesis of anthraquinones and tetracenediones by using ʟ-proline as organocatalyst and benzoic acid as additive (Scheme 40) [74]. They

• -trimethoxybenzaldehyde also afforded the corresponding para-adducts 189 in different proportions in the reaction mixture. As expected, when the authors used aliphatic aldehydes, they did not detect the corresponding derivatives 188 [79]. Other procedures In 2009, Naeimi and Namdari published a one-pot synthesis of

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

Asymmetric organocatalyzed synthesis of coumarin derivatives

• Natália M. Moreira,
• Lorena S. R. Martelli and
• Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

• obtained with good to excellent yields and enantiomeric excesses. Besides, the one-pot synthesis of coumarins followed by the Michael addition step was proven to be a good alternative, affording the desired product with excellent yield and ee. The applicability of the methodology was also demonstrated by a

• intermediate and the coumarin through hydrogen bonding, as shown in Scheme 25. An enantioselective one-pot synthesis of spiro[dihydrofurocoumarin/pyrazolone] 83 mediated by quinine and squaramide catalyst 84 was reported by Xu et al. [61]. The work draws attention for the wide range of compounds obtained with

Development of N-F fluorinating agents and their fluorinations: Historical perspective

• Teruo Umemoto,
• Yuhao Yang and
• Gerald B. Hammond

Beilstein J. Org. Chem. 2021, 17, 1752–1813, doi:10.3762/bjoc.17.123

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

• Pezhman Shiri,
• Ali Mohammad Amani and
• Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

• (hetero)arylboronic acid 111 was reported. The use of a catalytic amount of CuCl and MeOLi as base in CH3CN as solvent was recognized as the optimized conditions. This strategy provided a new procedure for the one-pot synthesis of fully decorated 1,2,3-triazole derivatives 112 in good to excellent yield

Synthesis of functionalized imidazo[4,5-e]thiazolo[3,2-b]triazines by condensation of imidazo[4,5-e]triazinethiones with DMAD or DEAD and rearrangement to imidazo[4,5-e]thiazolo[2,3-c]triazines

• Alexei N. Izmest’ev,
• Dmitry B. Vinogradov,
• Natalya G. Kolotyrkina,
• Angelina N. Kravchenko and
• Galina A. Gazieva

Beilstein J. Org. Chem. 2021, 17, 1141–1148, doi:10.3762/bjoc.17.87

• imidazo[4,5-e]thiazolo[3,2-b]triazines 4a–n into imidazo[4,5-e]thiazolo[2,3-c]triazines 5a–n. One-pot synthesis of compounds 5a,b,h,i from imidazo[4,5-e]triazines 3a,b. Plausible mechanism of the formation and the rearrangement of compounds 4 into isomers 5. Results for the screening of the reaction

Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

• Asha Budakoti,
• Pradip Kumar Mondal,
• Prachi Verma and
• Jagadish Khamrai

Beilstein J. Org. Chem. 2021, 17, 932–963, doi:10.3762/bjoc.17.77

• allylisilane 152. Further manipulation of functional groups of 153 leads to the synthesis of (−)-dactyloide (Scheme 36) [71]. The one-pot synthesis of a 2,6-disubstituted THP was reported by Minehan and co-workers and involved treating 3-iodo-2-[(trimethylsilyl)methyl]propene with an aldehyde in the presence

• Alder’s chair-like transition state 227 in which the (Z)-alkene accounts for the trans-stereocontrol at the C3 position and equatorial iodide addition accounts for the cis-stereocontrol at the C4 position, as shown below in Scheme 54. The one-pot synthesis of tetrahydropyran by utilizing the Babier–Prins

Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines

• Geetanjali S. Sontakke,
• Rahul K. Shukla and
• Chandra M. R. Volla

Beilstein J. Org. Chem. 2021, 17, 485–493, doi:10.3762/bjoc.17.42

• isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-triazoles. A variety of α-triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and

• derivatives, we performed a sequential one-pot synthesis by combining a Cu(I)-catalyzed “Click” reaction of phenylacetylene (7) with TsN3 and a metal-free C2-heteroarylation of quinoline N-oxide (1a, Scheme 6b). Remarkably, the yield of the desired product 3a in the one-pot synthesis (80%) was comparable to

• isoquinoline N-oxide. Gram-scale and one-pot synthesis. Proposed mechanism. Optimization of the reaction conditions.a Supporting Information Supporting Information File 220: Experimental details. Funding The activity was generously supported by Science and Engineering Research Board (SERB), India: CRG/2019

Decarboxylative trifluoromethylthiolation of pyridylacetates

• Ryouta Kawanishi,
• Kosuke Nakada and
• Kazutaka Shibatomi

Beilstein J. Org. Chem. 2021, 17, 229–233, doi:10.3762/bjoc.17.23

• lithium pyridylacetates undergo decarboxylative fluorination upon treatment with an electrophilic fluorination reagent to afford fluoromethylpyridines under catalyst-free conditions. Furthermore, we demonstrated the one-pot synthesis of fluoromethylpyridines from methyl pyridylacetates by saponification

• , entry 11). In the absence of MS 4 Å, the yield of 2a was diminished even when the reaction was carried out in THF (Table 1, entry 12). With the optimized reaction conditions in hand, we examined the one-pot synthesis of 2a from methyl ester 7a. Methyl 2-pyridylacetate 7a were saponified with lithium