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DOI: 10.1039/A705531E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 807-812

The preparation of some 1,7b-disubstituted cyclopropa[c]isoquinolines via nitrile ylide cyclisations and their rearrangement to 2-benzazepines and 4-alkenyl-1,4-dihydroisoquinolines

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Jon-Paul Strachan, John T. Sharp and Simon Parsons

Abstract

Diene-conjugated nitrile ylides of the type 1a, having substituents other than hydrogen in the R1 position, cyclise normally to give the C-7b substituted cyclopropa[c]isoquinolines 2a. In cases where R2 or R3 = H the latter undergo the usual thermal rearrangement to give 5-substituted 2-benzazepines 5a. However, when R2 and R3 ≠ H and either is a CH3 group, then the presence of the C-7b substituent in 2a diverts the thermal rearrangement into a new reaction path leading to the formation of 1,4-dihydro-4-alkenylisoquinolines 14 in high yield.

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