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Paper | Regular issue | Vol 57, No. 10, 2002, pp.1831-1840
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9551
Synthesis of Some Thiophene-fused Azepino[5,4,3-cd]indoles

Basem A. Moosa, Kayed A. Abu Safieh, and Mustafa M. El-Abadelah*

*Chemistry Department, Faculty of Science, University of Jordan, Amman 11942, Jordan


Interaction of indolylzinc chloride with 2-chloro-3-nitrothiophene gave 3-(3-nitrothien-2-yl)indole (7) which was converted, via reduction followed by acylation, into 3-(3-acylaminothien-2-yl)indoles (9a-c). Cyclization of 9a-c induced by phosphorus oxy-chloride under Bischler-Napieralski reaction conditions, took place regioselectively at the indolic C-4 locus to furnish the respective thieno[2’,3’ : 6,7]azepino[5,4,3-cd]indoles (3a-c).