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■ Fischer Indolization of the Phenylhydrazones from 3-Ethyl- and 3-(2-Methylpropyl)-substituted 1,3,4,6,7,11b-Hexahydroxy-9,10-dimethoxy-2H-benzo[a]quinolizin-2-one. Identification of the indole[1’,2’:3,4]pyrimido[6,1-a]isoquinoline Skeleton

Jonathan B. Ball. John B. Bremner, and Elaine J. Browne

*Department of Chemistry, University of Tasmania, GPO Box 252C Hobart, Tasmania, 7001, Australia

Abstract

A Fischer idolization of the phenylhydrazone (2a) derived from 3-ethyl-1,3,4,6,7, 11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizin-2-one (1a) gave the three products (3a), (4a) and (5a). The identity of (3a) and (4a) as diastereomeric benz[a]indolo[2,3-h]quinolizine derivatives was confirmed, but the third product, previously assigned the benz[a]indolo[3,2-g]quinolizine structure (6a), was identified as the indolo[1’,2’ :3,4]pyrimido[6,1-a]isquinoline derivative (5a), a representative of a new ring system. Similar results were obtained from the 3-(2-methylpropyl)- analogue (1b) (“Tetrabenazine”) of the ketone (1a); indolization of its phenylhydrazone (2b) gave rise to (3b), (4b) ard (5b).