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Note | Regular issue | Vol 53, No. 2, 2000, pp.433-439
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8774
Reactions of 1,2-Dimethyl-3-arylsulfonyl-4,5-dihydro-3H-imidazol-1-ium Iodides with Bifunctional Nucleophiles

Peiwen Zhou,* Bingjun Zhao, Jianxin Chen, Hongxing Wang, Congmin Kang, and Chizhong Xia

*Prolinx, Inc. 22322 20th Avenue, SE, Bothell, WA 98021, U.S.A.


The reaction of imidazolium salts, represented by 1,2-dimethyl-3-arylsulfonyl-4,5-dihydro-3H-imidazol-1-ium iodides (16), with two types of bifunctional nucleophiles: ortho-substituted anilines and ethylenediamine was studied. Their reactions with 1,2-phenylenediamine, 2-aminophenol, and 2-aminothiophenol resulted in exclusively one-carbon unit transfer products: 2-methylbenzoxazole (7), 2-methylbenzimidazole (8), and 2-methylbenzothiazole (9) respectively, which mimics the one-carbon unit transfer reaction of N (5), N (10)-methenyltetrahydrofolate coenzyme. The reaction of imidazolium (3, 4, and 6) with ethylenediamine exclusively produced the bis-adducts of two equivalents of imidazolium iodides with one equivalent of ethylenediamine: N-methyl-N-(2-arylsulfonylamino)ethyl -N’-[2-(N’-2-arylsulfonylaminoethyl -N’-methyl)ethylideneamino]ethylacetamidine bishydroiodides (1012) respectively. These different behaviors were explained with addition reaction mechanism.