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

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

Volume: 22 Issue: 9

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

Affiliation:

• Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest,Hungary

• Hungarian Academy of Sciences, Research Centre for Natural Sciences, 1519 Budapest,Hungary

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

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.

Cite this article as:

Haraszti Flora , Igricz Tamas , Keglevich Gyorgy *, Milen Matyas and Abranyi-Balogh Peter*, Synthetic and Mechanistic Study on the Microwave Assisted Fries Rearrangement of 1-Methylidene-3,4-dihydroisoquinoline-2(1H)-yl-methanones, Current Organic Chemistry 2018; 22 (9) . https://dx.doi.org/10.2174/1385272822666180122155416