Divergent Access to Imidazopyrazinones and Imidazodiazepinones by Regioswitchable Post-Ugi Heteroannulation

A metal-free expeditious strategy for the divergent synthesis of structurally diverse bicyclic imidazo[1,5-a]pyrazine and imidazo[1,5-a][1,4]diazepine scaffolds is disclosed by combining an Ugi four-component reaction of easily available building blocks and an exo/endo selectivity-switchable post-Ugi intramolecular heterocyclization. Using PPh3, the intramolecular umpolung aza-Michael addition is mediated to selectively generate imidazopyrazinones through a 6-exo-dig cyclization, while without PPh3 fused imidazodiazepinones are obtained through a thermal 7-endo-dig cyclization in moderate yields. © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Авторы
Wu D.1 , Zhang X.1 , Li Y.1 , Ying S.1 , Zhu L.1 , Li Z.2 , Yang G.1 , Van Der Eycken E.V.
Язык
Английский
Статус
Опубликовано
Год
2019
Организации
  • 1 College of Pharmaceutical Science, Zhejiang University of Technology, 18 Chaowang Road, Hangzhou, 310014, China
  • 2 Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC) |||Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, Heverlee, 3001, Belgium
  • 3 Peoples Friendship University of Russia (RUDN University), Moscow, 117198, Russian Federation
Ключевые слова
Divergent synthesis; Imidazole; Nitrogen heterocycles; Phosphines; Ugi reaction
Дата создания
24.12.2019
Дата изменения
24.12.2019
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/55459/
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