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[3 + 2]-Annulations of N-Hydroxy Allenylamines with Nitrosoarenes: One-Pot Synthesis of Substituted Indole Products

Author:
Sharma, Pankaj, Liu, Rai-Shung
Source:
Organic letters 2016 v.18 no.3 pp. 412-415
ISSN:
1523-7052
Subject:
bioactive compounds, chemical reactions, chemical structure, oxygen, synthesis, toluene
Abstract:
In the presence of O₂ and an IPrCuCl additive (5 mol %), [3 + 2]-annulation reactions of N-hydroxyaniline with nitrosobenzenes in cold toluene form isoxazolidin-5-ol derivatives. Heating the same reaction mixture with DBU in toluene affords highly functionalized indole products efficiently. This method provides short synthesis of several bioactive molecules including WIN 48098, WIN 53365, and JWH 015.
Agid:
5792277