Synthetic and mechanistic study on the microwave assisted fries rearrangement of 1-methylidene-3,4-dihydroisoquinoline-2(1H)-yl-methanones

Flóra Haraszti, Tamás Igricz, G. Keglevich, Mátyás Milen, Péter Ábrányi Balogh

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Abstract

Formerly, an unexpected acyl migration of 1-methylidene-3,4-dihydroisoquinoline- 2(1H)-yl-methanone derivatives was observed, and on this basis a microwave assisted synthetic method was developed for the preparation of members of the 2’-(3,4- dihydroisoquinoline-1-ylidene)-1-ethan-1-one family, potential CB2 receptor agonists and PDE7 inhibitors. The reaction mechanism was studied with experimental and theoretical methods in order to propose intra- and intermolecular radical pathways.

Original languageEnglish
Pages (from-to)912-922
Number of pages11
JournalCurrent Organic Chemistry
Volume22
Issue number9
DOIs
Publication statusPublished - Jan 1 2018

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Keywords

  • Acylation
  • Fries-rearrangement
  • Isoquinolines
  • Mechanism
  • Microwave synthesis
  • Quantum chemistry
  • Radicals

ASJC Scopus subject areas

  • Organic Chemistry

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