One-carbon homologation of aldehydes to N-(α-haloacyl)benzotriazoles

Alan R. Katritzky, Srinivasa R. Tala, Sandeep K. Singh

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11 Scopus citations

Abstract

One-carbon homologated N-(α-haloacyl)benzotriazoles have been synthesized from the corresponding aromatic and aliphatic aldehydes. Vinylbenzotriazoles, prepared by the reaction of aldehydes with the one-carbon synthon BtCH2P+Ph3Cl-, were subsequently treated with Br2/Et3N to give 1-bromovinylbenzotriazoles. These were then treated with NBS/NIS in CH 3CN-H2O to furnish one-carbon homologated N-(α-haloacyl)benzotriazoles in 53-77% yields. We have also demonstrated the utility of these new reagents in organic synthesis.

Original languageEnglish (US)
Pages (from-to)3231-3237
Number of pages7
JournalSynthesis
Issue number19
DOIs
StatePublished - Oct 4 2006

Keywords

  • Acylation
  • Aldehyde
  • Homologation
  • N-acylbenzotriazole
  • N-halosuccinimide

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