Bj. Zhao et al., SYNTHESIS AND CARBON UNIT TRANSFER-REACTIONS OF METHYL-SUBSTITUTED N-5,N-10-METHENYL-TETRAHYDROFOLATE COENZYMES, Gaodeng xuexiao huaxue xuebao, 19(7), 1998, pp. 1095-1100
Acetamide reacts with 1,2-diaminoethane to yield diacyl ethylenediamin
e , and the consecutive reaction with magnesium and m(or p) -nitrophen
ylsulfonyl chloride and methyl iodide gives 1,2-dimethyl-3-m(or p) -ni
trophenylsulfonyl imidazolinium salts that serve as the models of N-5,
N-10-C+R-tetrahydrofolate (THF) coenzymes(2a, 2b). The latter salts w
ith monofunctional nitrogen nucleophiles (p-methyl aniline, p-methoxy
aniline and so on) and carbon nucleophiles (malononitrile) give the in
termediate of ethylidyne transfer reaction. Bifunctional nucleophiles
(1, 2-diaminobenzene, 8-aminophenol) react with 2a and 2b to yield eth
ylidyne transfer products.