Journal
SYNTHESIS-STUTTGART
Volume 45, Issue 15, Pages 2120-2124Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0032-1316859
Keywords
pyridine alkaloids; iridium; microwave; green chemistry; N-heterocyclization
Categories
Funding
- National Institute on Drug Abuse [DA023916]
- Louisiana Board of Regents through the Board of Regents Support Fund [LEQSF (2009-12)-RD-A-26]
- University of New Orleans
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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%.
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