Synthesis of 3-Bromoindenes from 4-Alkynyl Alcohols/Sulfonamides and Aldehydes via Prins Cyclization, Ring-Opening and Friedel-Crafts Reactions

Trimurtulu Kotipalli, Duen Ren Hou

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Abstract

A one-pot, two-staged protocol has been developed for the synthesis of 3-bromoindenes from aryl alkynyl alcohols/sulfonamides and aldehydes. Bromotrimethylsilane (TMSBr) initiated a halo-Prins cyclization reaction to give 3-(bromomethylene)-tetrahydropyrans or -piperidines, which underwent ring-opening and Friedel-Crafts allylation to yield 3-bromoindenes in the presence of Brønsted acids.

Original languageEnglish
Pages (from-to)1561-1571
Number of pages11
JournalAsian Journal of Organic Chemistry
Volume8
Issue number8
DOIs
StatePublished - Aug 2019

Keywords

  • alkynes
  • cascade reactions
  • cyclization
  • Friedel-Crafts
  • indenes

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