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Unexpected Ring Opening During the Imination of Camphor‐Type Bicyclic Ketones
Author(s) -
Chernyshov Vladimir V.,
Yarovaya Olga I.,
Vatsadze Sergey Z.,
Borisevich Sophia S.,
Trukhan Sergey N.,
Gatilov Yuri V.,
Peshkov Roman Yu.,
Eltsov Ilia V.,
Martyanov Oleg N.,
Salakhutdinov Nariman F.
Publication year - 2021
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.202001397
Subject(s) - chemistry , bicyclic molecule , camphor , ring (chemistry) , heteroatom , regioselectivity , bond cleavage , stereochemistry , imide , reaction mechanism , medicinal chemistry , organic chemistry , catalysis
A new ring opening reaction was found while attempting to isolate the imines from ortho ‐heteroatom substituted anilines and camphor‐like bicyclic ketones. The benzoazoles containing a cyclopentanemethyl group at position 2 of the heterocycle were isolated instead of the expected imines. The detailed study of the transformation, including EPR experiments, revealed the most probable radical mechanism. The proposed reaction pathways were confirmed by quantum chemical calculations. The dichotomy of 1–2 and 2–3 bonds cleavage is discussed together with the evaluation of the stereochemical outcome of the reactions. The benzoazoles obtained via the new reaction are of particular interest for the medicinal chemistry.