The literature of heterocyclic chemistry, part XXII, 2022

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

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N-Acyl-1,2,3-triazoles – key intermediates in denitrogenative transformations

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(61), P. 9364 - 9367

Published: Jan. 1, 2023

N -Acyl-1,2,3-triazoles were fully characterized and their role in denitrogenative transformations was demonstrated.

Language: Английский

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Recent advances in the synthetic applications of Morita–Baylis–Hillman and Rauhut–Currier adducts of nitroalkenes

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(31), P. 6243 - 6262

Published: Jan. 1, 2023

This article reviews the recent applications of Morita–Baylis–Hillman and Rauhut–Currier adducts nitroalkenes. It also covers mechanistic aspects, including key intermediates reaction pathways.

Language: Английский

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Synthesis of N-vinyl isothiocyanates and carbamates by the cleavage of NH-1,2,3-triazoles with one-carbon electrophiles

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(6), P. 1143 - 1147

Published: Jan. 1, 2023

Metal-free cascade reaction of NH-1,2,3-triazoles with one-carbon electrophiles, such as thiophosgene and triphosgene, led to N-vinylated ring cleavage products. Using this approach the synthesis N-vinylisothiocyanates from NH-triazoles was achieved. A variety multifunctional compounds, N-vinylcarbamates, unsymmetrical vinylureas, carbamothioates, etc. prepared by a one-pot method NH-triazoles, triphosgene nucleophiles.

Language: Английский

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Recent Advances in the Synthesis of Nitrogen Heterocycles Using β-Nitrostyrenes as Substrates

Current Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(2), P. 108 - 118

Published: Jan. 1, 2023

Abstract:: The exploration of synthetic methodologies that allow rapid access to a wide variety N-heterocycles is critical importance the medicinal chemist as it provides ability expand available drug-like chemical space and drives more efficient drug discovery programs. β-Nitrostyrenes, unique active intermediates, have been widely applied in organic chemistry because their versatile utility pharmaceutical agents agrochemicals. In this review, we summarize recent development application elegant methods enable concise synthesis from β-nitrostyrenes various partners step- atom-economic manner, including cascade reactions, C-H activation, regio- stereoselective syntheses, well other novel which will potentially provide useful insights for further exploring designing reactions.

Language: Английский

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1-Aryl-3-nitro- and 3-Bromo-3-nitroprop-2-en-1-ones: Synthesis and Structural Features

Russian Journal of General Chemistry, Journal Year: 2024, Volume and Issue: 94(3), P. 497 - 507

Published: March 1, 2024

Abstract A method for producing a number of ( E )-1-aryl-3-nitroprop-2-en-1-ones based on synthetic condensation–dehydration strategy has been optimized. New Z )-1-aryl-3-bromo-3-nitroprop-2-en-1-ones have synthesised from using halogenation-dehydrohalogenation to )-1-aryl-3-nitroprop-2-en-1-ones. The fine structure nitro- and bromonitroenketones it’s features were determined by 1 H– H NOESY NMR X-ray diffraction analysis.

Language: Английский

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NH-1,2,3-triazoles as versatile building blocks in denitrogenative transformations

RSC Advances, Journal Year: 2023, Volume and Issue: 13(49), P. 34646 - 34651

Published: Jan. 1, 2023

The utilization of NH-1,2,3-triazoles as easily accessible building blocks in denitrogenative ring cleavage transformations with electrophiles to provide multifunctionalized nitrogen heterocycles and N -alkenyl compounds is reviewed.

Language: Английский

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Synthesis and Characterization of Multiple Functionalized Cyclohexanone Using Diels–Alder Reaction of α-Nitrocinnamate

Reactions, Journal Year: 2022, Volume and Issue: 3(4), P. 615 - 624

Published: Dec. 2, 2022

A systematic study of the Diels–Alder reaction α-nitrocinnamate was performed. The p-substituted with 2,3-dimethyl-1,3-butadienes smoothly proceeded regardless p-substituent, which either an electron-donating or -withdrawing group. control revealed that isomerized during reaction. Danishefsly’s diene (1-methoxy-3-trimethylsiloxy-1,3-butadiene) facilitated cycloaddition under mild conditions to afford a cycloadduct without alternation diastereomeric ratio. Moreover, desilylation furnished multiple functionalized cyclohexanones.

Language: Английский

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Metal‐Free [2+3] Dipolar Cycloaddition/Denitration Cascade between Nitroalkenes and α‐Diazoesters: Regioselective Access to Functionalized NH−Pyrazoles

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(6)

Published: April 3, 2024

Abstract An efficient one‐pot synthesis of 1 H ‐pyrazoles has been realized via cascade cyclocondensation β‐nitroalkenes as C2 synthon with α‐diazoesters C1N2 unit. The reaction proceeds concomitant formation two new (C−N & C−C) bonds in one stretch leading to ethyl‐5‐nitro‐4‐phenyl‐4,5‐dihydro‐3 ‐pyrazole‐3‐carboxylate intermediate, which undergoes base mediated denitration enabling the NH−pyrazoles. This protocol not only features easy operation, catalyst−free conditions, good high yields, wide scope and late‐stage functionalization, but also opens up a avenue for synthetically demanding structurally non‐traditional pyrazoles. A combination experimental DFT studies provide evidence proposed mechanism.

Language: Английский

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HFIP-Mediated Synthesis of 4-Aryl-NH-1,2,3-Triazoles and 1,5-Disubstituted 1,2,3-Triazolyl Glycoconjugates

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 7, 2024

We herein report a multicomponent reaction for the synthesis of

Language: Английский

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