53703-88-1Relevant academic research and scientific papers
"All-water" chemistry of tandem N-alkylation-reduction- condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles
Kommi, Damodara N.,Kumar, Dinesh,Bansal, Rohit,Chebolu, Rajesh,Chakraborti, Asit K.
, p. 3329 - 3335 (2013/01/16)
A water-assisted tandem N-alkylation-reduction-condensation process has been devised as a new synthetic route for the one-pot synthesis of N-arylmethyl-2-substituted benzimidazoles. Water plays the crucial and indispensable role through hydrogen bond mediated 'electrophile-nucleophile dual activation' in promoting selective N-monobenzylation of o-nitroanilines as an alternative to the transition metal-based chemistry for C-N bond formation (amination) and forms the basis of disposing the substituents on the benzimidazole moiety in regiodefined manner. Water also exerts a beneficial effect in the condensation of N-monobenzylated o-phenylenediamines with aldehydes. The water-assisted C-N bond formation chemistry led to metal/base-free synthesis of N-monobenzylated o-nitroanilines and N-monobenzylated o-phenylenediamines. The indispensable/advantageous role of water in the various stage of the N-alkylation-reduction-condensation process exemplifies an 'all-water' chemistry for the synthesis of N-arylmethyl-2- substituted benzimidazoles.
Pyrolysis of N1,N3-Disubstituted 5-Methyl- and 5-Chlorobenzimidazolines
Chalapathi Rao, C. V.,Kondal Reddy, K.,Rao, N. V. Subba
, p. 967 - 969 (2007/10/02)
The pyrolysis of 2-aryl-1-benzyl-3,5-dimethyl(I)-, 5-chloro-3-methyl(II)-, 3-substituted-benzyl-5-methyl(III)- and 3-substituted-benzyl-5-chloro-(IV)-benzimidazolines has been carried out to study the orientation of their elimination reactions.The benzyl group is eliminated in preference to methyl in benzimidazolines of the types (I) and (II) irrespective of the nature of the substituent in phenylene and aryl moieties.The course of the elimination reaction in compounds of the types (III) and (IV) appears to be determined by the relative stabilities of benzyl and substituted benzyl radicals.The structures of the pyrolysis products have been established on the basis of spectral and chemical evidences.
