82775-86-8Relevant academic research and scientific papers
Simultaneous Formation and Functionalization of Aryliminophosphoranes Using 1,3-Dihydro-1 H-benzimidazol-2-ones as Precursors
Pattarawarapan, Mookda,Yamano, Dolnapa,Wiriya, Nittaya,Yimklan, Saranphong,Phakhodee, Wong
, p. 13330 - 13338 (2020)
An atom- and step-economic synthesis of aryliminophosphoranes bearing ortho urea was achieved via unprecedented Ph3P-I2 mediated ring-opening of 1,3-dihydro-1H-benzimidazol-2-ones with secondary amines. Tandem aza-Wittig/heterocyclization of the functionalized aryliminophosphoranes upon treatment with isothiocyanates enables a facile access to a single regioisomer of N1-substituted 2-aminobenzimidazoles as well as fused tetracyclic quinazolinone derivatives in one-pot. 31P{1H} NMR studies suggested that the urea C-N bond of benzimidazolone is weakened by N-phosphorylation, leading to aminolysis rather than the expected deoxygenative amination.
Photochemistry, of Heterocyclics. III. Photolysis of Various 2-Substituted Benzimidazoles
Crank, George,Mursyidi, Achmad
, p. 775 - 784 (2007/10/02)
A variety of 2-substituted benzimidazoles have been irradiated with ultraviolet light to determine the effects of substituents on the photochemical behaviour of the benzimidazole ring system.Benzimidazol-2-amine gave -2'amine and -2'-amine, showing that this derivative behaves in the same way as benzimidazole. 2-Chlorobenzimidazole loses chlorine forming a dimeric species and benzimidazol-2(3H)-one, which is itself inert to photolysis. 2-Trichloromethylbenzimidazole also loses chlorine to form a variety of products depending on the solvent. 2-Trifluoromethylbenzimidazole does not lose fluorine but forms a dimer and also undergoes imidazole ring cleavage.Benzimidazole-2-thiol also undergoes imidazole ring cleavage with loss of sulfur.The 2-phenyl group stabilizes the benzimidazole ring system to photolysis as does the 2-thiazolyl group; however, the latter suffers thiazole ring cleavage.
