19382-37-7Relevant academic research and scientific papers
Electrocatalytic Intermolecular C(sp3)-H/N-H Coupling of Methyl N-Heteroaromatics with Amines and Amino Acids: Access to Imidazo-Fused N-Heterocycles
Qian, Peng,Yan, Zicong,Zhou, Zhenghong,Hu, Kangfei,Wang, Jiawei,Li, Zhibin,Zha, Zhenggen,Wang, Zhiyong
supporting information, p. 6359 - 6363 (2018/10/20)
An efficient NH4I-mediated intermolecular annulation of methyl N-heteroaromatics with amines/amino acids was developed by virtue of anodic oxidation, providing a variety of functionalized imidazo-fused N-heterocycles with good to excellent yields. The practicality of this protocol was demonstrated by the readily available starting materials, broad substrate scope, water tolerance, scalability, and the diverse transformations of the electrolysis product.
Triflic anhydride mediated synthesis of imidazo[1,5-a]azines
Pelletier, Guillaume,Charette, Andre B.
supporting information, p. 2290 - 2293 (2013/06/26)
Imidazo[1,5-a]azines are synthesized in moderate to excellent yields using a mild cyclodehydration/aromatization reaction triggered by the use of triflic anhydride (Tf2O) and 2-methoxypyridine (2-MeOPyr). Various substitution patterns and functional groups were found to be compatible under the optimized conditions. In addition, a 5-bromo-3-aryl derivative was also shown to be active in a Sonogashira cross-coupling and direct arylation reactions. A tertiary amide was compatible as a substrate leading to the synthesis of an imidazo[1,5-a]pyridinium triflate.
Natural α-amino acids applied in the synthesis of imidazo[1,5-a ]N-heterocycles under mild conditions
Wang, Qiang,Zhang, Shuai,Guo, Fengfeng,Zhang, Baiqun,Hu, Ping,Wang, Zhiyong
, p. 11161 - 11166 (2013/02/22)
A facile iodine-mediated decarboxylative cyclization from α-amino acids and N-heterocyclic carbaldehydes was developed. By virtue of this method, a series of imidazo[1,5-a]N-heterocycles can be synthesized efficiently under mild conditions. A tentative re
Studies on Wallach's Imidazole Synthesis
Benincori, Tiziana,Brenna, Elisabetta,Sannicolo, Franco
, p. 675 - 680 (2007/10/02)
The reaction of the N-benzylamides of N-heterocyclic carboxylic acids 3 and 6-9 with phosphorus pentachloride affords heterocondensed imidazoles 4 and 10-14 by a scheme reminiscent of Wallach's imidazole synthesis starting from N,N'-dialkyloxamides.Kinetic and labelling experiments are described which support a mechanism involving nitrile ylide species and allow a better understanding of the Wallach reaction.The limiting parameter for the formation of heteroanellated imidazoles is the electron availability of the heterocyclic ring.
