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Synthesis 2003(9): 1367-1372
DOI: 10.1055/s-2003-40207
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2-Alkenyl-1-pyrrolin-1-oxides and Polysubstituted Nitrones

Cecília P. Sára, József Jekőb, Kálmán Hideg*a
a Institute of Organic and Medicinal Chemistry, University of Pécs, 7602 Pécs, P.O. Box 99, Hungary
Fax: +36(72)536219; e-Mail: kalman.hideg@aok.pte.hu;
b ICN Hungary Ltd., 4440 Tiszavasvári, P.O. Box 1, Hungary
Further Information

Publication History

Received 2 March 2003
Publication Date:
24 June 2003 (online)

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Abstract

A new approach for the synthesis of α-hydroxy nitroxide ester 4 by oxidation of the sterically hindered amine 3 is described. The reaction of 2-methyl-1-pyrrolin-1-oxides 1 and 7 with aldehydes 5a-j gave 2-alkenyl nitrones, which could be converted to higher methylated 2-alkenyl DMPO type nitrones 11d or pyrrolidine nitroxides 12b,c,d,g,h,i with MeMgI.

Key words

aldol reactions - free radicals - Grignard reactions - ring opening

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