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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