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Communication | Regular issue | Vol 16, No. 9, 1981, pp.1449-1452
Published online, 1st January, 1970
DOI: 10.3987/R-1981-09-1449
Reaction of Phenacyldimethylsulfonium Iodine with o-Phenylenediamines

Shinzo Kano* and Yoko Yuasa

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


The reaction of o-phenylenediamine with phenacyldimethylsulfonium iodide gave 2-phenylquinoxaline. The same reaction by use of 3,4-diaminotoluene and 1,2-diamino-4-chlorobenzene instead of o-phenylenediamine afforded a mixture of the corresponding 6- and 7-substituted 2-phenylquinoxalines. In the case of 1,2-diamino-4-nitrobenzene, 6-nitro-2-phenylquinoxaline was obtained. On the other hand, the reaction of 1,2-diamino-4-methoxybenzene and phenacyldimethylsulfonium iodide gave 7-methoxy-2-phenylquinoxaline. Furthermore, condensation of maleonitrile with phenacyldimethylsulfonium iodide gave 2,3-dicyano-6-phenylpyrazine.