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Synthesis 2017; 49(10): 2286-2296
DOI: 10.1055/s-0036-1588411
DOI: 10.1055/s-0036-1588411
paper
Reactions of o-Quinone Methides with Halogenated 1H-Azoles: Access to Benzo[e]azolo[1,3]oxazines
Further Information
Publication History
Received: 18 November 2016
Accepted after revision: 13 January 2017
Publication Date:
02 February 2017 (online)
Abstract
A simple route to the series of azolo-condensed benzo[e][1,3]oxazines such as 9H-benzo[e][1,2,4]triazolo[5,1-b][1,3]oxazines, 9H-benzo[e]pyrazolo[5,1-b][1,3]oxazines, and 5H-benzo[e]imidazo[2,1-b][1,3]oxazines has been developed. The reaction proceeds through formation of an ortho-quinone methide intermediate followed by aza-Michael addition of the halogenoazoles to the o-quinone methide and intramolecular nucleophilic substitution.
Key words
quinone methide - 1H-azoles - cascade reactions - aza-Michael reaction - benzo[e]azolo[1,3]oxazinesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588411.
- Supporting Information
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