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Paper | Regular issue | Vol 51, No. 5, 1999, pp.1035-1050
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8477
Pyridazines, 89. On the Synthesis of Novel 1,2-Diazine Containing Tricyclic Systems: Preparation of Dipyridazinodiazepinones

Gottfried Heinisch, Elisabeth Huber, Barbara Matuszczak,* and Kurt Mereiter

*Institute of Pharmaceutical Chemistry, University of Innsbruck, Innrain 52a, A-6020 Innsbruck, Austria

Abstract

A synthetic method for the so far unknown dipyridazino[4,3-b:3’,4’-e][1,4]diazepinone system (7a) was elaborated. Cyclisation of 6-chloro-N-(3,6-dichloropyridazin-4-yl)-3-(4-methoxybenzylamino)-N-propylpyridazine-4-carbox-amide (5) under basic conditions was found to yield in addition to the expected compound (7a) an isomeric dipyridazino[3,4-b:3’,4’-e][1,4]diazepinone (7b) resulting from Smiles rearrangement. The 7a/7b ratio was found to be influenced by the nature of the base and the solvent.