Direct interaction of indolylzinc chloride with 2,5-dichloro-3,4-dinitrothiophene (4) produced 2,5-bis(indol-3- yl)-3,4-dinitrothiophene (5) together with 3-(5-chloro-3,4-dinitrothien-2-yl)indole (6). Interaction of the latter compound with 1-methylpiperazine gave 3-[4,5-di(4-methylpiperazin-1-yl)-3-nitrothien-2-yl]indole (7), as the expected SN-Ar (addition-elimination) di-substitution product, together with 3-[5-(4-methylpiperazin-1-yl)-3-nitrothien-2-yl]indole (8), a mono-substituted product. The formation of 8 probably proceeds via an anomalous pathway, related to cine-substitution, with departure of the nitro group at C-4. Compound 4 underwent SN-Ar substitution reaction with 1-methylpiperazine to give the respective 2,5-di-(4-methylpiperazin-1-yl)-2,4-dinitrothiophene (9).
Keywords: 2,5-bis(3-indolyl) thiophenes, 3-(5-chloro-3,4-dinitrothien-2-yl)indole, 2,5-dichloro-3,4-dinitrothiophene, 2,5-di-(4-methylpiperazin-1-yl)-2,4-dinitrothiophene, Indolylzinc chloride, SN-Ar reaction, Bis(indolyl)alkaloids, metabolites, pyrazinone, pyrimidine
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