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Paper | Regular issue | Vol 38, No. 8, 1994, pp.1845-1858
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6753
Inverse-Electron-Demand Diels-Alder Reactions of Condensed Pyridazines, 4. Synthesis and Cycloaddition Reactions of 1,4-Bis(trifluoromethyl)pyrido[3,4-d]pyridazine

Nobert Haider,* Kurt Mereiter, and Richard Wanko

*Institute of Pharmaceutical Chemistry, University of Vienna, Währinger Straße 10, A-1090 Vienna, Austria


The title compound (8) was prepared by a [4+2] cycloaddition reaction of 3,6-bis(trifluoromethyl)-1,2,4,5-tetrazine (1) with a 4-piperidone-derived enamine and subsequent aromatization of the tetrahydro compound (7). The azadiene reactivity of 8 was investigated employing enamines and a ketene-N,S-acetal as electron-rich dienophiles. A series of new condensed isoquinolines (10, 11, 12a,b, 13) was obtained and one of them (13) was characterized by X-ray structure determination.