138479-55-7Relevant academic research and scientific papers
Transition-metal-free insertion of benzyl bromides into 2-(1H-benzo[d]imidazol-1-yl)benzaldehyde: One-pot switchable syntheses of benzo[4,5]imidazo[1,2-a]quinolin-5(7H)-ones and 3-arylquinolin-4-ones mediated by base
Xu, Huayan,Xu, Liang,Luo, Xiaowei,Wang, Junfeng,Zhou, Xuefeng,Yang, Bin,Li, Ding,Luo, Zaigang,Liu, Yonghong,Liao, Shengrong
, p. 2785 - 2796 (2019)
A transition-metal-free insertion of benzyl group between aldehyde and imidazole of 2-(1H-benzo[d]imidazol-1-yl)benzaldehyde was achieved for the first time. Two diverse sets of quinolin-4-one derivatives: benzo[4,5]imidazo[1,2-a]quinolin-5(7H)-ones (2) and 3-arylquinolin-4-ones (3) were synthesized based on identical starting materials 2-(1H-benzo[d]imidazol-1-yl)benzaldehydes (1) and benzyl bromides. In the preparations, two key intermediates I and II were involved and might be synthesized in situ through the reaction of an intra-Breslow intermediate with benzyl bromide via an enol attack in the presence of base or a NHC-based enamine attack in the absence of base, respectively, in which the intra-Breslow intermediate might function as a nucleophilic reagent by following two novel different pathways.
Rapid Access to Benzimidazo[1,2- a]quinoline-Fused Isoxazoles via Pd(II)-Catalyzed Intramolecular Cross Dehydrogenative Coupling: Synthetic Versatility and Photophysical Studies
Sahoo, Subrata,Pal, Shantanu
, p. 4081 - 4097 (2021/04/02)
An efficient and atom-economical palladium-catalyzed intramolecular cross dehydrogenative coupling (CDC) reaction has been developed for the construction of highly π-conjugated benzimidazo[1,2-a]quinoline-fused isoxazole scaffolds using molecular oxygen as sole oxidant. The approach portrayed wide substrate scope with good functional group tolerance and depicted a useful tool for the generation of fluorescence active compounds with high quantum yield. Synthetic versatility of the method via Fe-catalyzed reductive isoxazole ring cleavage toward pyridine, pyrimidine, pyrazole fused heteropolycyclic compounds has been showcase.
Cyclization Reactions in Azole Chemistry: The Reaction of Some Azoles with o-Fluoroacetophenone, o-Fluorobenzaldehyde and o-Fluorobenzophenone
Rosevear, Judi,Wilshire, John F. K.
, p. 1097 - 1114 (2007/10/02)
The reactions of some azoles with o-fluoro-acetophenone, -benzaldehyde and -benzophenone in dimethyl sulfoxide solution in the presence of anhydrous potassium carbonate have been investigated.In addition to the expected substitution products, cyclization
