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Issue 36, 2014
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Combinatorial synthesis of nicotine analogs using an Ugi 4-CR/cyclization-reduction strategy

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Abstract

A practical one-pot synthesis of nicotine analogs from Ugi 4-CR/propargyl adducts is reported. This methodology allows the rapid construction of the pyrrolidine moiety present in nicotine through an intramolecular base-promoted 5-endo cycloisomerization process, followed by a reduction of the resulting mixture of 2- and 3-pyrrolines to afford nicotine analogs in good overall yields.

Graphical abstract: Combinatorial synthesis of nicotine analogs using an Ugi 4-CR/cyclization-reduction strategy

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Article information


Submitted
11 Apr 2014
Accepted
11 Jul 2014
First published
14 Jul 2014

Org. Biomol. Chem., 2014,12, 7068-7082
Article type
Paper

Combinatorial synthesis of nicotine analogs using an Ugi 4-CR/cyclization-reduction strategy

L. A. Polindara-García and A. Vazquez, Org. Biomol. Chem., 2014, 12, 7068
DOI: 10.1039/C4OB00767K

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