… in heterocyclic synthesis: a novel translocation of an (N-amino-N-methylamino) methylene group from a heterocyclic N-amino-N-methylformamidine side chain to the …

RS Hosmane, BB Lim, FN Burnett

Index: Hosmane, Ramachandra S.; Lim, Benjamin B.; Burnett, Friedrich N. Journal of Organic Chemistry, 1988 , vol. 53, # 2 p. 382 - 386

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Citation Number: 37

Abstract

Our studies began with the reagent methyl N-(dicyanomethyl) me thanimidate [(CN) 2CHN= CHOMe] which was prepared by an improvement of the literature procedure previously reported for the analogous ethyl ester. 6* 6 The above reagent, upon treatment with benzylamine, afforded 5-amino-l-benzyl-4-cyanoimidazole in nearly quantitative yield. Further reaction of the latter with trimethyl orthoformate, catalyzed by trifluoroacetic acid, ...