New Facile Synthesis of 3,4-Dihydroquinazoline-2(1H)-thiones by a Sequential Ugi-Azide/Staudinger/Aza-Wittig/Cyclization Reaction

Author:

Xiong Jun12,Min Qing1,Yao Gang1,Zhang Jia-An1,Yu Hai-Feng1,Ding Ming-Wu2ORCID

Affiliation:

1. School of Pharmacy, Hubei University of Science and Technology

2. Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University

Abstract

A new facile synthesis of 3,4-dihydroquinazoline-2(1H)-thiones by an Ugi-azide/Staudinger/aza-Wittig/cyclization sequence has been developed. The Ugi-azide reactions of 2-azidobenzaldehydes, amines, trimethylsilyl azide, and isocyanides produced tetrazoles, which, when treated with methyldiphenylphosphane and CS2, produced 3,4-dihydroquinazoline-2(1H)-thiones in good overall yields via a sequential Staudinger/aza-Wittig/cyclization reaction.

Funder

National Natural Science Foundation of China

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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