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Synthesis 2009(16): 2679-2688  
DOI: 10.1055/s-0029-1216871
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Copper-Catalyzed Synthesis of 2-Amino-4(3H)-quinazolinone and 2-Aminoquinazoline Derivatives

Xuhu Huanga,b, Haijun Yanga, Hua Fu*a, Renzhong Qiao*b, Yufen Zhaoa
a Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
Fax: +86(10)62781695; e-Mail: fuhua@mail.tsinghua.edu.cn;
b State Key Laboratory of Chemical Resource Engineering, Department of Pharmaceutical Engineering, College of Life Science and Technology, Beijing University of Chemical Technology, Beijing 100029, P. R. of China
e-Mail: qiaorz@mail.buct.edu.cn;
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Publication History

Received 10 March 2009
Publication Date:
26 June 2009 (online)

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Abstract

We have developed a versatile and efficient method for copper-catalyzed synthesis of both 2-amino-4(3H)-quinazolinone and 2-aminoquinazoline derivatives. The protocol uses readily available substituted 2-halobenzoic acids, 2-bromobenzaldehyde, 2-bromophenyl ketones and guanidines as the starting materials, inexpensive copper(I) iodide as the catalyst, and the method has important application values for construction of N-heterocycles in organic chemistry and medicinal chemistry.

Key words

copper-catalyzed - cross-coupling - 2-amino-4(3H)-quinazolinone - 2-aminoquinazoline - synthetic method