10406-94-7Relevant articles and documents
C2-Selective Branched Alkylation of Benzimidazoles by Rhodium(I)-Catalyzed C-H Activation
Tran, Ga?l,Confair, Danielle,Hesp, Kevin D.,Mascitti, Vincent,Ellman, Jonathan A.
, p. 9243 - 9252 (2017/09/11)
Herein, we report a Rh(I)/bisphosphine/K3PO4 catalytic system allowing for the first time the selective branched C-H alkylation of benzimidazoles with Michael acceptors. Branched alkylation with N,N-dimethyl acrylamide was successfully applied to the alkylation of a broad range of benzimidazoles incorporating a variety of N-substituents and with both electron-rich and -poor functionality displayed at different sites of the arene. Moreover, the introduction of a quaternary carbon was achieved by alkylation with ethyl methacrylate. The method was also shown to be applicable to the C2-selective branched alkylation of azabenzimidazoles.
Supercritical methanol as solvent and carbon source in the catalytic conversion of 1,2-diaminobenzenes and 2-nitroanilines to benzimidazoles
Sun, Zhuohua,Bottari, Giovanni,Barta, Katalin
, p. 5172 - 5181 (2015/12/08)
Benzimidazoles and N-methylbenzimidazoles were synthesized by simply heating 1,2-diaminobenzenes in supercritical methanol over copper-doped porous metal oxides. These catalysts were derived from synthetic hydrotalcites that only contain earth-abundant starting materials. The carbon equivalents needed for the construction of the benzimidazole core originated from the solvent itself, which is known to undergo reforming to hydrogen and carbon monoxide through the formation of a formaldehyde intermediate. A variety of 1,2-diaminobenzenes were converted to the corresponding mixtures of benzimidazoles and N-methylated analogues in good yields. Interestingly, the more challenging, but readily available 2-nitroanilines, which require an additional reduction step prior to cyclization, could also be successfully converted to benzimidazoles in high selectivity. Furthermore, various other alcohols were applied besides methanol, to obtain 2-alkyl- and 1,2-dialkylbenzimidazoles. Preliminary mechanistic insights into the origins of N-alkylation as well as the reactivity of the nitro derivatives are discussed.
A mild, one-pot synthesis of disubstituted benzimidazoles from 2-nitroanilines
Hornberger, Keith R.,Adjabeng, George M.,Dickson, Hamilton D.,Davis-Ward, Ronda G.
, p. 5359 - 5361 (2007/10/03)
A one-pot synthesis of disubstituted benzimidazoles from 2-nitroanilines is described. Hydrogenation of N-substituted 2-nitroanilines with palladium on carbon as catalyst in the presence of trimethyl orthoformate and catalytic pyridinium p-toluenesulfonate (PPTS) at room temperature provided good to excellent yields of the corresponding disubstituted benzimidazoles.