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Paper | Regular issue | Vol 75, No. 12, 2008, pp.3015-3024
Published online, 28th July, 2008
DOI: 10.3987/COM-08-11472
Novel and Efficient Access to Thieno[3,4-c]cinnolines

Karine Gehanne, Jean-Charles Lancelot, Stéphane Lemaître, Hussein El-Kashef, and Sylvain Rault*

*Centre d’Etudes et de Recherche sur le Médicament de Normandie UPRES EA 4258 PR CNRS INC3M - Université de Caen Basse-Normandie, U.F.R. des Sciences Pharmaceutiques, 5, rue Vaubénard - 14032 Caen, France


New substituted methyl thieno[3,4-c]cinnoline-3-carboxylate compounds were synthesized from the corresponding methyl 3-aminothiophene-2-carboxylate precursors by a new route using a modified Sandmeyer reaction. Under proper conditions, Sandmeyer reaction led to the formation of thieno[3,4-c] cinnoline compounds by a regioselective intramolecular cyclization, instead of the expected substitution of the amino group by a bromine atom.