Tetrahedron letters

Vicarious nucleophilic substitution of 1-benzyl-5-nitroimidazole, application to the synthesis of 6, 7-dihydroimidazo [4, 5-d][1, 3] diazepin-8 (3H)-one

BC Chen, ST Chao, JE Sundeen, J Tellew, S Ahmad

Index: Chen, Bang-Chi; Chao, Sam T.; Sundeen, Joseph E.; Tellew, John; Ahmad, Saleem Tetrahedron Letters, 2002 , vol. 43, # 9 p. 1595 - 1596

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Citation Number: 15

Abstract

Reaction of 1-benzyl-5-nitroimidazole with carbanion generated from chloroform and potassium tert-butoxide afforded 1-benzyl-4-dichloromethyl-5-nitroimidazole in 72% yield. This vicarious nucleophilic substitution reaction was successfully applied to the synthesis of 6, 7-dihydroimidazo [4, 5-d][1, 3] diazepin-8 (3H)-one, an important intermediate in the synthesis of natural and biologically active compounds.