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

[ Vol. 22 , Issue. 9 ]

Author(s):

Flora Haraszti, Tamas Igricz, Gyorgy Keglevich*, Matyas Milen and Peter Abranyi-Balogh*   Pages 912 - 922 ( 11 )

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.

Affiliation:

Hungarian Academy of Sciences, Research Centre for Natural Sciences, 1519 Budapest, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Egis Pharmaceuticals Plc., Directorate of Drug Substance Development, 1475 Budapest, Hungarian Academy of Sciences, Research Centre for Natural Sciences, 1519 Budapest

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