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Synfacts 2009(12): 1332-1332  
DOI: 10.1055/s-0029-1218226
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Synthesis of 2H-1,4-Benzoxazin-3-(4H)-ones

Contributor(s): Victor Snieckus, Johnathan Board
D. Chen, G. Shen, W. Bao*
Zhejiang University, Hangzhou and Taizhou University, Linhai, P. R. of China
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Publication History

Publication Date:
20 November 2009 (online)

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Significance

Reported is the copper-catalyzed synthesis of substituted 2H-1,4-benzoxazin-3-(4H)-ones from 2-halophenols and acetamides. The first step is postulated to be a Cs2CO3-mediated nucleophilic displacement of the aliphatic ­halide (X²) by the phenol to give intermediate A, examples of which were isolated. This then undergoes an Ullmann-type coupling to give the final products.

Review: J. Ila, P. tefani¡c Anderluh, M. Sollner Dolenc, D. Kikelj Tetrahedron 2005, 61, 7325-7348.

Book: H. Ulrich, In Science of Synthesis, Vol. 17; S. M. Weinreb, Ed.; Georg Thieme Verlag: Stutt­gart, New York, 2004, 58-78.