4.5 Article

Syntheses of 4-Substituted 2-(Trichloromethyl) quinazolines under Mild Conditions by Benzyne [4+2] Cycloaddition

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 27, Pages 5910-5913

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402706

Keywords

Synthetic methods; Cycloaddition; Fused-ring systems; Nitrogen heterocycles; Benzyne

Funding

  1. Secretaria de Investigacion y Estudios Avanzados - Universidad Autonoma del Estado de Mexico (SIEA-UAEMex) [3532/2013]

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An experimentally simple and convenient synthesis of 4-susbstituted 2-(trichloromethyl)quinazolines by cycloaddition of benzyne with 2-(trichloromethyl)-1,3-diazabutadienes was developed. The 2-(trichloromethyl)-1,3-diazabutadienes (R-1 = H and Me) were prepared from trichloroacetamidine and the appropriate N,N-dimethylamide dimethyl acetal or from trichloroacetamidine and a Vilsmeier-Haack reagent containing an aryl group.

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