55233-64-2Relevant academic research and scientific papers
A new method for the synthesis of 2-aryl-1H-benzimidazoles: Selenium-catalyzed reductive N-heterocyclization of benzylidene(2-nitroaryl) amines with carbon monoxide
Nishiyama, Yutaka,Fujimoto, Mayu,Sonoda, Noboru
, p. 109 - 111 (2006)
The treatment of benzylidene(2-nitroaryl)amines, prepared by the reaction of o-nitro aniline and benzaldehydes, with carbon monoxide in the presence of a catalytic amount of selenium under basic conditions, afforded 2-aryl-1H-benzimidazoles in moderate to good yields. Georg Thieme Verlag Stuttgart.
Palladium-Catalyzed Formation of N-Heteroarenes from Nitroarenes using Molybdenum Hexacarbonyl as the Source of Carbon Monoxide
Zhou, Fei,Wang, Duo-Sheng,Driver, Tom G.
supporting information, p. 3463 - 3468 (2016/01/25)
The development of a method that employs a two-chamber reaction vessel and uses molybdenum hexacarbonyl [Mo(CO)6] as the carbon monoxide (CO) source for the palladium-catalyzed transformation of nitroarenes into indoles or imidazoles is reported.
Microwave-assisted Cadogan reaction for the synthesis of 2-aryl-2H-indazoles, 2-aryl-1H-benzimidazoles, 2-carbonylindoles, carbazole, and phenazine
Creencia, Evelyn Cuevas,Kosaka, Masahiro,Muramatsu, Toshikatsu,Kobayashi, Masashi,Iizuka, Tomohiro,Horaguchi, Takaaki
experimental part, p. 1309 - 1317 (2010/03/23)
(Chemical Equation Presented) The Cadogan reaction, a widely accepted route for the synthesis of nitrogen containing heterocycles, is modified by using microwave radiation as the source of heat instead of the conventional heating by reflux in a nitrogen atmosphere for several hours. Appropriate starting materials were mixed with triethyl phosphite or triphenylphosphine and irradiated with microwaves for several minutes at a specific power to give the desired products. The indazoles were prepared by irradiating N-(2-nitrobenzylidene) anilines with triethyl phosphite at 200 W for 12-14 min to give 85-92% product yields. Irradiation of the mixture of N-benzylidene-2-nitroanilines and triphenylphosphine at 200 W for 3-5 min yielded 93-96% of the benzimidazoles. The carbonylindoles were obtained in 61-68% yields by irradiating 2-nitrochalcone or alkyl 2-nitrocinnamates and triphenylphosphine with microwaves at 80-200 W for 8-11 min. The mixture of 2-nitrobiphenyl and triphenylphosphine yielded 96% of carbazole when irradiated with microwaves at 200 W for 2 min while 75% of phenazine was obtained by irradiating the mixture of 2-nitrodiphenylamine and triphenylphosphine with microwaves at 200 W for 3.5 min. These results show that microwave-assisted Cadogan reactions gave better product yields at shorter reaction times.
