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Paper | Regular issue | Vol 38, No. 8, 1994, pp.1805-1811
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6726
Inverse-Electron-Demand Diels-Alder Reactions of Condensed Pyridazines, 5. 1,4-Bis(trifluoromethyl)pyridazino[4,5-b]indole as an Azadiene

Norbert Haider* and Richard Wanko

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


The pyridazino[4,5-b]indole (3), which is conveniently available from 3-methylthioindole and the tetrazine (2), undergoes thermally induced inverse-electron-demand Diels-Alder reactions with enamines to afford the cycloalkene-annelated carbazoles (7,8) or the 2-substituted carbazole (9), respectively.