154927-05-6Relevant articles and documents
Synthesis of a new imidazo[4,5-b]pyridin-5-one via a vicarious nucleophilic substitution of hydrogen
Crozet, Maxime D.,Suspène, Clément,Kaafarani, Mustapha,Crozet, Michel P.,Vanelle, Patrice
, p. 1629 - 1635 (2007/10/03)
A new imidazo [4,5-b]pyridin-5-one was prepared in five steps from 4(5)-nitro-1H-imidazole via a vicarious nucleophilic substitution of hydrogen of 1-benzyl-4-nitro-1H-imidazole with the carbanion generated from chloroform and potassium tert-butoxide. Hydrolysis of 1-benzyl-5-dichloromethyl-4-nitro-1H- imidazole and Knoevenagel condensation between the resulting aldehyde and diethyl malonate catalyzed by titanium(IV) chloride gave the corresponding 4-nitroimidazole bearing at 4 position the diethyl methylenemalonate group. Reduction and cyclization afforded the required ethyl 1-benzyl-5-oxo-4,5- dihydro-1H-imidazo[4,5-b]pyridine-6-carboxylate.
Synthesis of Some New Imidazole Derivatives
Ostrowski, S.
, p. 2237 - 2248 (2007/10/02)
N-Protected (CH2Ph, CH3) 4-nitroimidazoles (1) react with carbanions of tert-butyl chloroacetate, chloroacetonitrile and chloroform, affording Vicarious Nucleophilic Substitution of Hydrogen (VNS) products 2, 3, and 7, respectively.These compounds, after