Synthesis 2007(12): 1779-1784  
DOI: 10.1055/s-2007-983714
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Novel Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazolines by the Regioselective Cyclization of 1,4-Disubstituted Thiosemicarbazides

Dexin Feng, You Huang*, Ruyu Chen*, Yaqin Yu, Haibin Song
Institute of Elemento-Organic Chemistry, National Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China
Fax: +86(22)23503627; e-Mail: hyou@nankai.edu.cn;
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Publikationsverlauf

Received 31 January 2007
Publikationsdatum:
08. Juni 2007 (online)

Abstract

A novel and efficient route for the regioselective synthesis of 5-aryl-2-[(4-aryl-2-oxo-1,3,2-dioxaphosphinan-2-yl)imino]-2,3-dihydro-1,3,4-oxadiazoles in high yield and purity by the de­sulfurization and cyclization of 1-benzoyl-4-[(4-aryl-2-oxo-1,3,2-dioxaphosphinan-2-yl)thiosemicarbazides under mild conditions is reported. The products are isolated as the trans-isomer only.