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Thursday 14 January 2016

(4 - methoxyphenyl)(2 - methyl - 1 - (2 - morpholinoethyl) - 1H - indol - 3 - yl)methanone
















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

Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, R.O.C.
Org. Lett., Article ASAP
DOI: 10.1021/acs.orglett.5b03447
Publication Date (Web): January 8, 2016
Copyright © 2016 American Chemical Society

Abstract

Abstract Image
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

http://pubs.acs.org/doi/abs/10.1021/acs.orglett.5b03447
http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.5b03447/suppl_file/ol5b03447_si_001.pdf
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