Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-: C] quinolines

The polyphosphoric acid-mediated reaction of 2-(2-aminophenyl)indenes with nitroalkenes was tested in the frame of synthetic studies towards CDK inhibitors with the paullone core. Unexpectedly, this reaction proceeded via a different mechanistic pathway affording derivatives of the natural alkaloid isocryptolepine. The scope of this unusual transformation was investigated and a mechanistic rationale explaining this outcome is offered. This journal is © The Royal Society of Chemistry.

Авторы
Aksenov A.V.1 , Aksenov D.A.1 , Griaznov G.D.1, 2 , Aksenov N.A. 1 , Voskressensky L.G. 3 , Rubin M.1, 2
Издательство
Royal Society of Chemistry
Номер выпуска
23
Язык
Английский
Страницы
4325-4332
Статус
Опубликовано
Том
16
Год
2018
Организации
  • 1 Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol, 355009, Russian Federation
  • 2 Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr, Lawrence, KS 66045-7582, United States
  • 3 Department of Chemistry, Peoples' Friendship University of Russia, 6 Mikhluho-Maklaya St., Moscow, Russian Federation
Ключевые слова
Positive ions; CDK inhibitors; Mechanistic pathways; Mediated reactions; Nitroalkenes; Polyphosphoric acids; Synthetic study; Chemistry
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/7115/
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