Conversion of Bicyclic C-Azoaziridines to 2-Substituted 2H-1,2,3-triazoles

Triazole derivatives R 0280Conversion of Bicyclic C-Azoaziridines to 2-Substituted 2H-1,2,3-Triazoles. -Bicyclic C-azoaziridines (I), (III) and (V) are converted to triazoles (II), (IV) or (VI), resp,. in acidified chloroform solution or on the surface of silica gel. -(BUCHAKA, S. M.; KUZNETSOV, M. A.; SCHANTL, J. G.; Chem. Heterocycl. Compd. (N. Y.) 41 (2005) 10, 1321-1326; St. Petersburg State Univ., St. Petersburg 198504, Russia; Eng.) -R. Langenstrassen 24-135

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Conversion of Bicyclic C‐Azoaziridines to 2‐Substituted 2H‐1,2,3‐Triazoles.

Buchaka

Кузнецов

Schantl

2006

ChemInform

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Pyrazoles and C‐Imidoylaziridines through [4+1] Annulation and [2+1] Cycloaddition of 1‐Azabuta‐1,3‐dienes with a Synthetic Equivalent of Phthalimidonitrene

et al. 2017

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Oxidative addition of N‐aminophthalimide to 1,2,4‐triaryl‐1‐azabuta‐1,3‐dienes leads, in most cases, to the regiodefined formation of 1,3,5‐triarylpyrazoles in moderate to good yields through [4+1] annulation. This transformation is supposed to proceed by nitrenoid attack onto a lone pair of electrons of the imine nitrogen atom to give the vinylazomethine imine, followed by its 1,5‐electrocyclization into pyrazoline and further aromatization into pyrazole. Rare examples of 2‐imidoyl‐1‐phthalimidoaziridines that are formed by competitive [2+1] cycloaddition onto the C=C bond were isolated in low yields for 1‐azadienes with electron‐deficient aryl substituents at the imine nitrogen atom.

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Thermal Ring Expansion of 2‐Sulfonylimidoyl‐1‐phthalimidoaziridines into N‐Sulfonylimidazoles

2018

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The oxidative phthalimidoaziridination of conjugated unsaturated N‐sulfonylimines leads, in most cases, to di‐substituted, tri‐substituted and spiro‐fused imidoylaziridines in synthetically useful yields typically above 70 %. The latter are thermally transformed into di‐substituted, tri‐substituted, and condensed N‐sulfonylimidazoles. Interestingly, this ring expansion is accompanied by an intramolecular 1,3‐sulfonyl shift from one nitrogen atom to another.

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Conversion of Bicyclic C-Azoaziridines to 2-Substituted 2H-1,2,3-triazoles

Abstract: In an acidified chloroform solution, bicyclic C-azo-N-(N-hetaryl)aziridines are converted to bicyclic 2H-1,2,3-triazoles. This transformation can occur on the surface of silica gel, and also during storage of these compounds at room temperature.

Cited by 4 publications

References 9 publications