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.

Язык оригиналаанглийский
Страницы (с-по)452-463
Число страниц12
ЖурналEuropean Journal of Organic Chemistry
Номер выпуска3
Ранняя дата в режиме онлайн27 дек 2020
СостояниеОпубликовано - 22 янв 2021


Подробные сведения о темах исследования «Unexpected Ring Opening During the Imination of Camphor-Type Bicyclic Ketones». Вместе они формируют уникальный семантический отпечаток (fingerprint).