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■ Pentacyclic Phenothiazines I. Construction of the Pyrido[3’,4’:4,5]pyrrolo[3,2,1-kl]phenothiazine Ring System via Selective Metallation of a 2-Substituted Pyrrolo[3,2,1-kl]phenothiazine

Torsten Dahlgren, Donald R. Deardorff, and Arnold R. Martin

*Department of Pharmaceutical Sciences, College of Pharmacy, The University of Arizona, Tucson, AZ 85721, U.S.A.

Abstract

A new pentacyclic heterocycle, 3-benzyl-1,2,3,4-tetrahydro-4H-pyrido[3’,4’:4,5]pyrrolo[3,2,1-kl]phenotiazin-4-one (2), the first known example of the pyrido[3’,4’:4,5]pyrrolo[3,2,1-kl]phenothiazine ring system (1) has been prepared in seven steps beginning with pyrrolo[3,2,1-kl]phenothiazine (3). Key to the success of the synthesis is the selective metallation, and subsequent alkylation with ethylene oxide, of 2-[2-pyrrolo-[3,2,1-kl]phenothiazinyl]-4,4-dimethyl-2-oxazoline (10).