Synthesis 2012; 44(23): 3655-3660
DOI: 10.1055/s-0032-1317516
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Nitroxide-Annulated Carbocycles and Heterocycles

Tamás Kálai
a   Institute of Organic and Medicinal Chemistry, University of Pécs, Szigeti st. 12, 7624 Pécs, Hungary   Fax: +36(72)536219   Email: kalman.hideg@aok.pte.hu
c   Szentágothai Research Centre, Ifjúság st. 20, 7624 Pécs, Hungary
,
Balázs Bognár
a   Institute of Organic and Medicinal Chemistry, University of Pécs, Szigeti st. 12, 7624 Pécs, Hungary   Fax: +36(72)536219   Email: kalman.hideg@aok.pte.hu
,
Dániel Zsolnai
a   Institute of Organic and Medicinal Chemistry, University of Pécs, Szigeti st. 12, 7624 Pécs, Hungary   Fax: +36(72)536219   Email: kalman.hideg@aok.pte.hu
,
Zoltán Berente
b   Institute of Biochemistry and Medical Chemistry, University of Pécs, Szigeti st. 12, 7624 Pécs, Hungary
,
Kálmán Hideg*
a   Institute of Organic and Medicinal Chemistry, University of Pécs, Szigeti st. 12, 7624 Pécs, Hungary   Fax: +36(72)536219   Email: kalman.hideg@aok.pte.hu
› Author Affiliations
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Publication History

Received: 16 August 2012

Accepted after revision: 10 October 2012

Publication Date:
30 October 2012 (online)


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Dedicated to Prof. Péter Mátyus on the occasion of his 60th birthday

Abstract

New, pyrroline nitroxide annulated lactones, polycycles, and maleimide were synthesized by classical and microwave-assisted methodology. We report the application of the metathesis reaction in the presence of nitroxide yielding a pyrroline nitroxide condensed 1,4-benzoquinone as a paramagnetic dienophile. The formation of the isoselenazolone-fused pyrroline ring system was examined and different reactivity was observed with pyrrolin-1-oxyl and pyrroline derivatives.

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