CHEMISTRY OF APORPHINES .4. SYNTHESIS OF APORPHINES VIA REISSERT ALKYLATION, PHOTOCHEMICAL CYCLIZATION, AND PSCHORR CYCLIZATION ROUTE

Nitrobenzyl-(4b) and iodobenzylisoquinoline (4a) derivatives have been synthesized by the condensation of Reissert compounds (1) with nitrobenzyl (2b) and iodobenzyl chlorides (2a). Subsequent reduction and Pschorr cyclization of the nitrobenzylisoquinoline resulted in a facile route to the synthesis of aporphines (4b → 5b → 6c → 7). Photochemical cyclization of 1-(2-iodobenzyl)-2-methyl-1,2,3,4-tetrahydroisoqmnoline (6a → 7) also resulted in the isolation of aporphine, but in considerably lower yields. © 1969, American Chemical Society. All rights reserved.