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1. One-Pot Formation of Piperidine- and Pyrrolidine-Substituted Pyridinium Salts via Addition of 5-Alkylaminopenta-2,4-dienals to N-Acyliminium Ions: Application to the Synthesis of (±)-Nicotine and Analogs.

Author

Sabrina Peixoto, Tuan Minh Nguyen, David Crich, Bernard Delpech, and Christian Marazano

Subjects
*PIPERIDINE, *PYRROLIDINE, *PYRIDINIUM compounds, *ORGANIC synthesis, *NICOTINE, *RING formation (Chemistry), *CARBAMATES, *CHEMICAL reduction
Abstract

Addition of 5-alkylaminopenta-2,4-dienals onto N-acyliminium ions, generated in situ from α-hydroxycarbamates derived from pyrrolidine or piperidine, in the presence of zinc triflate, followed by dehydrative cyclization, allowed the formation of pyridinium salts substituted at their 3-position by a five- or six-membered nitrogen heterocycle. Subsequent N-dealkylation of the pyridinium moiety and deprotection of the secondary amine or reduction of the carbamate function led to (±)-nicotine and analogs. [ABSTRACT FROM AUTHOR]

Published
2010
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