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Thermal Ring Expansion of 2‐Sulfonylimidoyl‐1‐phthalimidoaziridines into N ‐Sulfonylimidazoles
Author(s) -
Stukalov Aleksandr,
Suslonov Vitalii V.,
Kuznetsov Mikhail A.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701806
Subject(s) - chemistry , intramolecular force , ring (chemistry) , sulfonyl , nitrogen atom , conjugated system , medicinal chemistry , nitrogen , stereochemistry , organic chemistry , polymer , alkyl
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.