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Ring Expansion of Tetrahydroisoquinolines to Form Benzoazocines
L. G. Voskressensky*, A. V. Listratova, T. N. Borisova, G. G. Alexandrov, A. V. Varlamov
Peoples’ Friendship University of Russia, Moscow, Russia
21 February 2008 (online)
Reported is a synthesis of azocines from tetrahydroisoquinolines by ring expansion using an activated alkyne. A mechanism is proposed which involves initial formation of a zwitterion species (structure A above) by Michael addition of the tertiary amine to an alkyne, followed by a mechanistically unknown rearrangement to afford the azocine.