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Synthesis 2013; 45(15): 2120-2124
DOI: 10.1055/s-0032-1316859
special topic
© Georg Thieme Verlag Stuttgart · New York

Microwave-Assisted Iridium-Catalyzed Synthesis of Nicotine and Anabasine Derivatives

Tushar Dattu Apsunde
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA   Fax: +1(504)2806860   Email: mtrudell@uno.edu
,
Mark L. Trudell*
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA   Fax: +1(504)2806860   Email: mtrudell@uno.edu
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Further Information

Publication History

Received: 20 December 2012

Accepted after revision: 31 January 2013

Publication Date:
27 February 2013 (online)

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Abstract

Various functionalized nicotine and anabasine analogues are synthesized via a three-step sequence that exploits a microwave-assisted iridium-catalyzed N-heterocyclization of 1,4- and 1,5-diols for the construction of the pyrrolidine and piperidine ring systems. The microwave-assisted N-heterocyclization furnishes derivatives of nicotine and anabasine in good yields (50–75%) with overall yields ranging from 30–50%.

Key words

pyridine alkaloids - iridium - microwave - green chemistry - N-heterocyclization

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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