Synthesis 2012; 44(22): 3447-3452
DOI: 10.1055/s-0032-1316794
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of New Thienopyridine Derivatives by [3+2]- and [2+2]-Cycloaddition Reactions

Mátyás Milen*
a  Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary
b  EGIS Pharmaceuticals PLC, Division for Chemical Research, P.O.B. 100, 1475 Budapest, Hungary   Fax: +36(1)4633648   Email: gkeglevich@mail.bme.hu
,
Péter Ábrányi-Balogh
a  Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary
,
András Dancsó
b  EGIS Pharmaceuticals PLC, Division for Chemical Research, P.O.B. 100, 1475 Budapest, Hungary   Fax: +36(1)4633648   Email: gkeglevich@mail.bme.hu
,
György Keglevich*
a  Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary
› Author Affiliations
Further Information

Publication History

Received: 16 July 2012

Accepted after revision: 17 September 2012

Publication Date:
02 October 2012 (online)


Abstract

The reaction of 6,7-dihydrothieno[3,2-c]pyridine derivatives with 1,3-dipoles, such as a nitrile oxides or nitrile imines, gave novel fused heterocycles. The Staudinger reaction of the starting material was also studied. This reaction was stereoselective and exclusively gave racemic cis-cycloadducts in which the thienopyridine core was fused with a β-lactam ring.

 
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