82040-13-9Relevant academic research and scientific papers
Fine tuning the outcome of 1,3-dipolar cycloaddition reactions of benzimidazolium ylides to activated alkynes
Georgescu, Emilian,Nicolescu, Alina,Georgescu, Florentina,Teodorescu, Florina,Shova, Sergiu,Marinoiu, Adriana T.,Dumitrascu, Florea,Deleanu, Calin
, p. 2507 - 2520 (2016/04/26)
1,3-Dipolar cycloaddition reactions of benzimidazolium ylides, generated from 3-phenacylbenzimidazolium bromides, to non-symmetrical activated dipolarophiles in various reaction conditions led to complex mixtures of pyrrolo[1,2-a]benzimidazole and pyrrolo[1,2-a]quinoxaline derivatives. In order to explain all experimental results, the influence of reaction conditions on the reaction products was investigated. For the first time, 4-hydroxy-4,5-dihydropyrrolo[1,2-a]quinoxaline derivatives 6, pyrrolo[1,2-a]quinoxalinium quaternary salts 8, as well as 4-methoxy-4,5-dihydropyrrolo[1,2-a]quinoxalines 9, were separated, fully characterized and their interconversions are presented, together with a proposed reaction mechanism.
Unusual cleavage of phenacyl-substituted benzimidazolium salts. Synthesis of 1,4-diarylimidazoles
Kuz'menko,Kuz'menko,Simonov,Korobov,Filippov
, p. 293 - 297 (2007/10/02)
The action of ammonium acetate in acetic acid on 1-alkyl(aralkyl)-3-phenacylbenzimidazolium bromides leads, in addition to the formation of a new imidazole ring, to cleavage of the benzimidazole fragment of the molecule at the 1,2 bond to give 1-alkyl(aralkyl)aminoaryl-4-arylimidazoles. 1,2-Dimethyl-3-(p-nitrophenacyl)benzimidazolium bromide is converted under similar conditions to the corresponding 2-methylimidazole. 4,4′-Dimethyl-2,2′-bis(p-nitrophenyl)-1,1′-dipyrrolo[1,2-a]benzimidazole was isolated as a side product of this reaction.
