[3+2] Anionic Cycloaddition of Isocyanides to Acyclic Enamines and Enaminones: A New, Simple, and Convenient Method for the Synthesis of 2,4-Disubstituted Pyrroles

We herein demonstrate a new approach for the synthesis of 2,4-disubstituted pyrroles by [3+2] cycloaddition reaction of isocyanides to the activated double bond of various enamines and enaminones. This process paved the way for the synthesis a series of 2,4-disubstituted pyrroles, which are known to be intermediates in the synthesis of biologically active compounds, in good to excellent yields from simple and commercially available starting materials. The process is carried out efficiently using a strong base, tBuOK, at low temperatures (0 °C). The described method is simple, proceeds in one step, does not require additional catalysts and hence, has a wide scope. © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Авторы
Efimov I.V. 1 , Matveeva M.D. 1 , Luque R. 1, 2 , Bakulev V.A.3 , Voskressensky L.G. 1
Номер выпуска
9
Язык
Английский
Страницы
1108-1113
Статус
Опубликовано
Том
2020
Год
2020
Организации
  • 1 Research Center: Molecular Design and Synthesis of Innovative Compounds for Medicine, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st, 6, Moscow, 117198, Russian Federation
  • 2 Departamento de Quimica Organica, Universidad de Cordoba, Campus de Rabanales, Edificio Marie Curie (C-3), Universidad de Cordoba, Ctra Nnal IV-A, Km 396, Cordoba, Spain
  • 3 Campus de Rabanales, Edificio Marie Curie (C-3), Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira st., Yekaterinburg, 620002, Russian Federation
Ключевые слова
Cycloaddition; Enamines; Enaminones; Isocyanides; Potassium tert-butoxide; Pyrroles
Дата создания
02.11.2020
Дата изменения
02.11.2020
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/64903/
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