Gold(I)-catalyzed 6-endo-dig hydrative cyclization of an alkyne-tethered ynamide: access to 1,6-dihydropyridin-2(3H)ones

Nayan Ghosh, Sanatan Nayak, Akhila K. Sahoo

Research output: Contribution to journalArticleOtherpeer-review

54 Citations (Scopus)

Abstract

Hydrate your chemistry! Hydrative cyclization of 5-yne-ynamides in the presence of Echavarren's catalyst and p-toluenesulphonic acid (PTSA)×H2O at room temperature affords an array of 1,6-dihydropyridin-2(3H)one derivatives. Isomerization, epoxidation, and hydrogenation of the double bond and insertion of an extended π-conjugate system into the pyridinone skeleton have been successfully accomplished (see scheme; Ts=tosyl).

Original languageEnglish
Pages (from-to)9428-9433
Number of pages6
JournalChemistry - A European Journal
Volume19
Issue number29
DOIs
Publication statusPublished - 15 Jul 2013
Externally publishedYes

Keywords

  • gold catalysis
  • heterocycles
  • hydrative cyclization
  • pyridinones
  • yne-ynamides

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