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

Authors

  • 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 Organic Chemistry Department, Belarusian State Technological University, 13a Sverdlova St., Minsk 220006

DOI:

https://doi.org/10.1007/6508

Keywords:

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

Abstract

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.

Author Biographies

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

Organic Chemistry Department

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Published

2022-05-18

Issue

Vol. 58 No. 4/5 (2022)

Section

Original Papers