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Communication | Special issue | Vol 11, No. 1, 1978, pp.387-399
Published online, 1st January, 1970
DOI: 10.3987/S(N)-1978-01-0387
Synthesis, Structure and Properties of Methyl-azuleno[1,8-cd]pyridazines

Klaus Hafner,* Hans Jörg Lindner, and Werner Wassem

*Institut für Organische Chemie, Technische Hochschule Darmstadt, Petersenstrasse. 22 D-6100 Darmstadt, Germany


N-Substituted 2H-cyclopenta[d]pyridazines (6) possessing methyl groups in 1- and/or 4-positions are easily deprotonated by strong bases to anions of type (7) which react with derivatives of β-dicarbonyl compounds to the substitution products (11) and (17). Cyclization of these in the presence of acids afford 1,3,5-trimethyl- and 1,3-dimethylazuleno[l,8-cd]pyridazine (12) and (18). The structure of the novel heterocyclic azulenes was determined by spectroscopic methods as well as by an X-ray analysis of (12).