G. Das, B. Choudhury, K. Das
Mar 1, 1999
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Journal
Journal of Chemical Research
Abstract
Among various bioactive heterocycles carbazole is an important nucleus. Reports on the biological activities of the 3-substituted and 3,6-disubstituted carbazoles are quite common in literature. 1 One method of inserting a functionality at the 3-position of carbazole is the Vilsmeier reaction, used by Buu-Hoi and Hoan to synthesize 3-formyl-9methylcarbazole.? In their process they used N-phenyl-Nmethyformanilide and phosphorus oxychloride to formylate 9-methylcarbazole at the 3-position in an a-dichlorobenzene medium. As it is not always possible to elucidate every aspect of the mechanism of an organic reaction experimentally, theoretical methods are necessary to understand it and to develop new approaches of synthesis. In this paper we have studied the mechanism of the formylation of 9-methylcarbazole using a semiempirical quantum mechanical method. We also report our experimental findings in obtaining 3,6-diformyl-9methylcarbazole along with 3-formyl-9-methylcarbazole while conducting a Vilsmeier reaction on 9-methylcarbazole.