424799-62-2Relevant academic research and scientific papers
Enantioselective C2-Allylation of Benzimidazoles Using 1,3-Diene Pronucleophiles
Knippel, James Levi,Ye, Yuxuan,Buchwald, Stephen L.
, p. 2153 - 2157 (2021)
Although substituted benzimidazoles are common substructures in bioactive small molecules, synthetic methods for their derivatization are still limited. Previously, several enantioselective allylation reactions of benzimidazoles were reported that functionalize the nucleophilic nitrogen atom. Herein we describe a reversal of this inherent selectivity toward N-allylation by using electrophilic N-OPiv benzimidazoles with readily available 1,3-dienes as nucleophile precursors. This CuH-catalyzed approach utilizes mild reaction conditions, exhibits broad functional-group compatibility, and exclusively forms the C2-allylated product with excellent stereoselectivity.
Synthesis of N-alkoxy-substituted 2H-benzimidazoles
Ansari, Nurul H.,S?derberg, Bj?rn C.G.
, p. 4717 - 4720 (2017/11/21)
Treatment of 2-nitro-N-(2-methyl-1-propen-1-yl)benzenamines with potassium tert-butoxide in tert-butanol followed by the addition of an electrophile affords N-alkoxy-2H-benzimidazoles. Electrophiles including methyl iodide, allylic bromides, propargylic bromides, benzyl bromide, and acetyl chloride gave good to excellent yields of product while 1-iodo- and 2-iodo-butane afforded very low yields.
Palladium-catalyzed synthesis of quinoxaline derivatives
Wallace, Jeffery M.,S?derberg, Bj?rn C.G.,Tamariz, Joaquín,Akhmedov, Novruz G.,Hurley, Mathew T.
, p. 9675 - 9684 (2008/12/22)
A palladium-catalyzed reductive N-heteroannulation of enamines derived from 2-nitrobenzenamines forming mixtures of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalin-2-ones is described. The reactions are performed using bis(dibenzylideneacetone)palladium(0), 1,3-bis(diphenylphosphino)propane, and 1,10-phenanthroline in DMF under 6 atm of carbon monoxide at 70 °C.
