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Letter

One-Step Synthesis of 3,5-Disubstituted-2-pyridylpyrroles from the Condensation of 1,3-Diones and 2-(Aminomethyl)pyridine

Supporting Info

Jamie J. Klappa, Autumn E. Rich, and Kristopher McNeill*

Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455

Org. Lett., 2002, 4 (3), pp 435–437

DOI: 10.1021/ol017147v

Publication Date (Web): January 11, 2002

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mcneill@chem.umn.edu

Abstract

3,5-Disubstituted- and 3,4,5-trisubstituted-2-(2-pyridyl)pyrroles may be synthesized efficiently from the novel condensation of 2-(aminomethyl)pyridine and 1,3-diones. The cyclization reaction was found to proceed through the intermediacy of a (2-pyridyl)methylimine. A marked dependence of the regioselectivity in the reaction of unsymmetrical diones on the presence of additional aminomethylpyridine suggests that two pathways to the product pyrroles are available.

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Published In Issue February 07, 2002
Received November 29, 2001

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Letter

One-Step Synthesis of 3,5-Disubstituted-2-pyridylpyrroles from the Condensation of 1,3-Diones and 2-(Aminomethyl)pyridine