Remarkable synergism in methylimidazole-promoted decarboxylation of substituted cinnamic acid derivatives in basic water medium under microwave irradiation: a clean synthesis of hydroxylated (E)-stilbenes

Vinod Kumar, Abhishek Sharma, Anuj Sharma, Arun K. Sinha

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

A metal-free protocol for decarboxylation of substituted α-phenylcinnamic acid derivatives in aqueous media is developed, wherein a remarkable synergism between methylimidazole and aq NaHCO3 in polyethylene glycol under microwave furnished the corresponding para/ortho hydroxylated (E)-stilbenes in a mild and efficient manner. The critical role of water in facilitating the decarboxylation imparts an interesting facet to the synthetic utility of water mediated organic transformations. The developed protocol provides a clean alternative to the hitherto indispensable multistep approaches involving toxic quinoline and a copper salt combination as the common decarboxylating agent.

Original languageEnglish
Pages (from-to)7640-7646
Number of pages7
JournalTetrahedron
Volume63
Issue number32
DOIs
StatePublished - 6 Aug 2007

Keywords

  • (E)-Stilbenes
  • Decarboxylation
  • Methylimidazole
  • Water chemistry
  • α-Phenylcinnamic acids

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