Denitrogenative Transformations of NH ‐ and N ‐Fluoroalkyl‐1,2,3‐triazoles DOI
Vladimir Motornov, Petr Beier

Published: Nov. 22, 2024

1,2,3-Triazoles with electron-acceptor groups on nitrogen, such as in situ acylated NH -triazoles or N -fluoroalkyl triazoles are amenable to denitrogenation thermally, using Brønsted Lewis acids, rhodium(II) catalysis. These cascade denitrogenations proceed via diazo intermediates followed by vinyl cations, rhodium carbene and lead various heterocyclic -alkenyl compounds.

Language: Английский

BF3·Et2O-promoted unconventional reactions of 2-oxoaldehyde: access to 4-amidooxazoles and β-keto amides/sulphonamides DOI

Ashiq Hussain Padder,

Bhawna Ghora,

Feroze Hussain

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This study investigates the potential of boron trifluoride etherate (BF3·OEt2) to trigger unprecedented reactions 2-oxoaldehydes with nitriles and amides/sulphonamides. In contrast mechanism in conventional reactions, α-carbonyl group induces a cyclization pathway be followed when reacting nitriles, yielding 4-amidooxazoles. Additionally, weak nucleophiles produce β-keto BF3·OEt2 catalysis offers novel, efficient, operationally simple synthetic route these valuable compounds, showcasing versatility Lewis acids organic transformations.

Language: Английский

Citations

0
Synthesis of N-vinyl isothiocyanates and carbamates by the cleavage of NH-1,2,3-triazoles with one-carbon electrophiles DOI Creative Commons
Vladimir Motornov, Petr Beier

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

Citations

6
NH-1,2,3-triazoles as versatile building blocks in denitrogenative transformations DOI Creative Commons
Vladimir Motornov, Petr Beier

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

Citations

3
Denitrogenative Transformations of NH ‐ and N ‐Fluoroalkyl‐1,2,3‐triazoles DOI
Vladimir Motornov, Petr Beier

Published: Nov. 22, 2024

1,2,3-Triazoles with electron-acceptor groups on nitrogen, such as in situ acylated NH -triazoles or N -fluoroalkyl triazoles are amenable to denitrogenation thermally, using Brønsted Lewis acids, rhodium(II) catalysis. These cascade denitrogenations proceed via diazo intermediates followed by vinyl cations, rhodium carbene and lead various heterocyclic -alkenyl compounds.

Language: Английский

Citations

0