title: Unexpected reactivity of o-nitrosophenol with RCH(2)Br: C-H bond cleavage and annulation to benzoxazoles and benzoxazines (R = Alkynyl).
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-CH(2)Br (R = aryl or vinyl) to give benzoxazoles with good functional group tolerance and high yield.
authors.affiliation: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.
authors.forename: Wei
authors.initials: W
authors.lastname: Yao
authors.forename: Dejian
authors.initials: D
authors.lastname: Huang