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Report | Regular issue | Vol 19, No. 10, 1982, pp.1895-1901
Published online, 1st January, 1970
DOI: 10.3987/R-1982-10-1895
Synthesis of Benzo[5,6]cyclohept[1,2,3ij]isoquinolines as Rigid Congeners of Tetrahydropapaveroline

Padam N. Sharma, Kenner C. Rice, and Arnold Brossi

*Medical Chemistry Section, Laboratory of Chemistry, NIDDK, National Institute of Health, Bethesda, MD 20892, U.S.A.

Abstract

The synthesis of several 5,6,9,10-tetraoxygenated 1,2,3,7 ,12,12a-hexahydrobenzo[5,6]cyclohept[l,2,3-ij]isoquinolines from (±)-coreximine (3) and its diacetate 4 is described. The secondary amine 8 afforded upon N-methylation the isoquinoline 7, previously obtained by Kametani et al through a different route. Aromatization of 8 afforded the aromatic isoquinoline 10 and O-demethylation of 8 with refluxing 48% HBr gave 9, a tetracyclic analog of tetrahydropapaveroline (THP).