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Paper | Regular issue | Vol 68, No. 12, 2006, pp.2549-2561
Published online, 31st October, 2006
DOI: 10.3987/COM-06-10879
Thermolysis of 5-Azido-4-arylpyridazin-3(2H)-ones: An Efficient and Versatile Synthesis of Pyridazino[4,5-b]indoles

Norbert Haider* and Andrea Wobus

*Department of Drug Synthesis, Faculty of Life Sciences, University of Vienna, Althanstrasse 14, A-1090 Vienna, Austria


5-Azido-4-arylpyridazin-3(2H)-ones, which are easily available from 4,5-dihalopyridazin-3(2H)-ones in few steps, were found to undergo in high yields a thermally induced cyclization into pyridazino[4,5-b]indole derivatives (“aza-carbolinones”) by formation of the N-5/C-5a bond via a nitrene insertion process. This new method is complementary to a previously reported pathway in which the C-4a/N-5 bond of the ring system is formed.