[3 + 2]-Annulations of N-hydroxy allenylamines with nitrosoarenes: One-pot synthesis of substituted indole products

Pankaj Sharma; Rai-Shung Liu

doi:10.1021/acs.orglett.5b03447

Back

[3 + 2]-Annulations of N-hydroxy allenylamines with nitrosoarenes: One-pot synthesis of substituted indole products

Journal article

Peer reviewed

[3 + 2]-Annulations of N-hydroxy allenylamines with nitrosoarenes: One-pot synthesis of substituted indole products

Pankaj Sharma and Rai-Shung Liu

Organic Letters, Vol.18(3), pp.412-415

05/02/2016

DOI: https://doi.org/10.1021/acs.orglett.5b03447

Abstract

In the presence of O ₂ 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.

Metrics

1 Record Views

See more details

Details

Title: [3 + 2]-Annulations of N-hydroxy allenylamines with nitrosoarenes: One-pot synthesis of substituted indole products
Creators - without role: Pankaj Sharma - National Tsing Hua University
Rai-Shung Liu - Department of Chemistry , National Tsing-Hua University
Publication Details: Organic Letters, Vol.18(3), pp.412-415
Identifiers: 9957773702806774
Academic Unit: Department of Chemistry, College of Science, National Tsing Hua University
Language: English
Resource Type: Journal article

[3 + 2]-Annulations of N-hydroxy allenylamines with nitrosoarenes: One-pot synthesis of substituted indole products

Abstract

Related links

Metrics

Details

National Tsing Hua University Social media