One-step synthesis of 3,5-disubstituted-2-pyridylpyrroles from the condensation of 1,3-diones and 2-(aminomethyl)pyridine

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

Research output: Contribution to journalArticlepeer-review

72 Scopus citations

Abstract

Equation Presented 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.

Original languageEnglish (US)
Pages (from-to)435-437
Number of pages3
JournalOrganic Letters
Volume4
Issue number3
DOIs
StatePublished - Feb 7 2002

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