相間移動触媒を用いたN-アルキル化反応 : N-アルキルシアノグアニジン誘導体の合体

概要

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It is known that the direct alkylation of cyanoguanidine by alkyl halide is very difficult because of the insolubility in organic solvents. We found that 1,1,3,3-tetrabenzyl-2-cyanoguanidine was obtained in good yield by the reaction of cyanoguanidine with benzyl chloride under phase transfer conditions. Further, when 1,3-dibromopropane was allowed to react with cyanoguanidine, the ring closure reaction on two amino groups of cyanoguanidine, was occurred to give 6-membered cyclic compound in low yield. However, it was found that N-alkylcyanoguanidines were used as the starting materials, cyclic compounds were obtained in good yields. Especially, the reactions of 1,4-dibromobutane with N-alkylcyanoguanidines gave N-alkyl-N', N'-tetramethylenecyanoguanidines, which were formed by the ring closure on one amino group, in high yields.
東海大学の論文