Alkylation of 5‐ and 6‐Methylindolo[2,3‐b]quinoxalines: Revised Structures of the N,N′‐Dimethylated Salts

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Abstract
N,N′‐Dialkylation of indolo[2,3‐b]quinoxaline could theoretically furnish three isomers, that is, salts dialkylated at the 5,6‐, the 6,11‐, and the 5,11‐positions. By using the 2,3‐dimethylated derivatives as models, the regioisomeric salts were selectively synthesized either by alkylation of the tetracycle or by cyclization of 1‐methylisatin with N,4,5‐trimethylbenzene‐1,2‐diamine. The structure of the N,N′‐dimethyl salts were unambiguously determined by NMR correlation sequences (1H‐1H NOESY, 1H‐13C HMQC, and 1H‐13C HMBC). The results of these studies show that the previous findings from the dialkylation of indoloquinoxaline need revision. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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