SYNTHESIS OF 1,2,6-TRISUBSTITUTED INDOLES FROM 6-PROPARGYLCYCLOHEX-2-ENONES AND PRIMARY AMINES

Авторы

  • Sergei G. Mikhalyonok Organic Chemistry Department, Belarusian State Technological University, 13a Sverdlova St., Minsk 220006
  • Nina M. Kuz'menok Organic Chemistry Department, Belarusian State Technological University, 13a Sverdlova St., Minsk 220006
  • Vladimir S. Bezborodov Organic Chemistry Department, Belarusian State Technological University, 13a Sverdlova St., Minsk 220006
  • Aliaksandr S. Arol Belarusian State Technological University

DOI:

https://doi.org/10.1007/6508

Ключевые слова:

cyclohex-2-enone, indole, air oxidation, amination–cyclization reaction

Аннотация

The synthesis of 1,2,6-trisubstituted indoles from accessible 6-propargylcyclohex-2-enones and primary amines is reported. Simple acidcatalyzed amination–cyclization reaction followed by air oxidation of the corresponding intermediated 4,5-dihydroindoles was found to be suitable to obtain the desired indoles. The reaction tolerates a variety of functional groups on the starting cyclohex-2-enones and primary amines. A mechanistic pathway involving nucleophilic addition/cyclization/aromatization is proposed.

Биографии авторов

Sergei G. Mikhalyonok, Organic Chemistry Department, Belarusian State Technological University, 13a Sverdlova St., Minsk 220006

Organic Chemistry Department

Nina M. Kuz'menok, Organic Chemistry Department, Belarusian State Technological University, 13a Sverdlova St., Minsk 220006

Organic Chemistry Department

Vladimir S. Bezborodov, Organic Chemistry Department, Belarusian State Technological University, 13a Sverdlova St., Minsk 220006

Organic Chemistry Department

Aliaksandr S. Arol, Belarusian State Technological University

Department of Organic Chemistry

PhD Student

Загрузки

Опубликован

2022-05-18

Выпуск

Том 58 № 4/5 (2022)

Раздел

Оригинальные статьи