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Paper | Regular issue | Vol 38, No. 10, 1994, pp.2267-2276
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6833
Cyclization Reactions of 2,2‘-Bis-N-methylindolyl to Potential Protein Kinase C Inhibitors

Ulf Pindur,* Young-Shin Kim, and Dieter Schollmeyer

*Department of Chemistry and Pharmacy, Institute of Pharmacy, University of Mainz, Saarstrasse 21, D-55122 Mainz, Germany

Abstract

2,2‘-Bis-N-methylindolyl (4) was used as the starting material in the syntheses of some indolo[2,3-a]carbazoles (6, 7, and 10a,b). Compounds of this type represent the subunit of the staurosporine group of substances, a natural class of protein kinase C inhibitors. Reaction of the bisindolyl (4) with 1,2,4,5-tetrazine-3,6-dicarboxylate — in the sense of a Diels-Alder reaction with inverse electron demand — gave rise to the pyridazino[b]indoles (11b,11b‘) as an isolable mixture of diastereomers and additionally to a rearranged product (13).