Pyrroles from ketoximes and acetylene. 22. Dihaloethanes in place of acetylene in reactions with cyclohexanone oxime

4,5,6,7-Tetrahydroindole and its 1-vinyl derivative were obtained in overall yields of 30–60% by the reaction of cyclohexanone oxime with 1,2-dichloro- and 1,2-dibromoethane in the MOH-dimethyl sulfoxide (DMSO) superbase system (M = K, Na, Li). Nucleophilic substitution of the halogen in the dihaloethanes by the oximate anion to give the corresponding ethylene glycol bis (imido ether) is a side reaction. The effect of the reaction conditions on the yields of products and the selectivity of the process was examined.See [1] for communication 21.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1202–1204, September, 1982.