Synthetic and Mechanistic Study on the Microwave Assisted Fries Rearrangement of 1-Methylidene-3,4-dihydroisoquinoline-2(1H)-yl-methanones

Author(s): Flora Haraszti, Tamas Igricz, Gyorgy Keglevich*, Matyas Milen, Peter Abranyi-Balogh*.

Journal Name: Current Organic Chemistry

Volume 22 , Issue 9 , 2018

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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.

Keywords: Isoquinolines, acylation, fries-rearrangement, microwave synthesis, mechanism, radicals, quantum chemistry.

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Article Details

VOLUME: 22
ISSUE: 9
Year: 2018
Page: [912 - 922]
Pages: 11
DOI: 10.2174/1385272822666180122155416

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