Unexpected reactivity of o-nitrosophenol with RCH2Br: C-H bond cleavage and annulation to benzoxazoles and benzoxazines (R = Alkynyl)

Please use this identifier to cite or link to this item: https://doi.org/10.1021/ol902812q

Title:	Unexpected reactivity of o-nitrosophenol with RCH2Br: C-H bond cleavage and annulation to benzoxazoles and benzoxazines (R = Alkynyl)
Authors:	Yao, W. Huang, D.
Issue Date:	19-Feb-2010
Citation:	Yao, W., Huang, D. (2010-02-19). Unexpected reactivity of o-nitrosophenol with RCH2Br: C-H bond cleavage and annulation to benzoxazoles and benzoxazines (R = Alkynyl). Organic Letters 12 (4) : 736-738. ScholarBank@NUS Repository. https://doi.org/10.1021/ol902812q
Abstract:	A one-pot reaction between two molecules of 5-diethylamino-2-nitrosophenol with one molecule of 2-butynyl bromide gave rise to a new heterocyclic compound (structure shown above) consisting of one benzoxazole and one benzoxazine ring. The reaction works equally well with 1-phenyl-3-chloro-1-propyne. It was also found that 5-diethylamino-2-nitrosophenol reacts with R-CH2Br (R = aryl or vinyl) to give benzoxazoles with good functional group tolerance and high yield. © 2010 American Chemical Society.
Source Title:	Organic Letters
URI:	http://scholarbank.nus.edu.sg/handle/10635/95376
ISSN:	15237060
DOI:	10.1021/ol902812q
Appears in Collections:	Staff Publications

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