Studies on the petasis reaction of 2-pyridinecarbaldehyde derivatives and its products

Hiroki Mandai, Kyouta Murota, Seiji Suga

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8 Citations (Scopus)

Abstract

The Petasis reaction of various 2-pyridinecarbaldehydes with secondary amines and boronic acids in refluxed acetonitrile proceeded to afford desired products up to 96% yield. The reaction proceeded under mild conditions to afford wide range of amines adjacent to heteroaromatic rings. Interestingly, the aldehyde possessing a nucleophilic moiety, 4-(dimethylamino)-2- pyridinecarbaldehyde, with (S)-(-)-N-methyl-1-phenylethylamine and 2 equivalent of trans-2-phenylvinylboronic acid afforded unexpected product, (E)-N-benzyl-3-phenyl-1-(pyridin-2-yl)prop-2-en-1-amine, in high yield. This product might be formed through the direct alkylation of aldehyde by trans-2-phenylvinylboronic acid, followed by anion/enolate isomerization. Derivatization of the Petasis products were also employed and 2-alkyl substituted pyridine derivatives can be obtained through deamination of the Petasis products under the simple hydrogenation conditions.

Original languageEnglish
Pages (from-to)1655-1669
Number of pages15
JournalHeterocycles
Volume85
Issue number7
DOIs
Publication statusPublished - 2012

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

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