3323-03-3Relevant academic research and scientific papers
Four-component synthesis of 3-aminomethylated imidazoheterocycles in EtOH under catalyst-free, oxidant-free and mild conditions
Gui, Qing-Wen,He, Wei-Min,Li, Fu-Long,Wang, Bin-Bin,Wu, Zhi-Lin,Yi, Min,Yu, Jia-Ling,Zhu, Meng-Xue,Zhu, Sha
supporting information, p. 4430 - 4434 (2021/06/30)
With green ethanol as the sole solvent, various 3-aminomethylated imidazoheterocycles were efficiently synthesized in one step through a four-component reaction of equimolar cheap and commercially available reactants at ambient temperature under metal-free, oxidant-free and mild conditions.
Use of imidazo[1,2-a]pyridine as a carbonyl surrogate in a mannich-like, catalyst free, one-pot reaction
Naresh, Gunaganti,Lakkaniga, Naga Rajiv,Kharbanda, Anupreet,Yan, Wei,Frett, Brendan,Li, Hong-Yu
, p. 770 - 777 (2019/01/14)
Derivatization of imidazo[1,2-a]pyridine scaffolds have gained considerable attention due to the biological significance of therapeutics based on the imidazopyridine core. By utilizing a catalyst-free, “Mannich type” reaction, we developed a simple and efficient protocol to aminomethylate the C-3 position of imidazo[1,2-a]pyridine through a multicomponent, de-carboxylation reaction involving imidazo[1,2-a]pyridine, a secondary amine, and glyoxylic acid. The developed protocol re-quires mild reaction conditions and furnishes diverse imid-azo[1,2-a]pyridine analogues from commercially available starting materials. Additionally, the current protocol improves prior methods, which were limited by the amine substrate scope. Taken together, this current methodology permits rapid diversification of imidazo[1,2-a]pyridines to enhance combinatorial efficiency in the drug discovery processes.
Discovery of new leads against Mycobacterium tuberculosis using scaffold hopping and shape based similarity
Wavhale, Ravindra D.,Martis, Elvis A.F.,Ambre, Premlata K.,Wan, Baojie,Franzblau, Scott G.,Iyer, Krishna R.,Raikuvar, Kavita,Macegoniuk, Katarzyna,Berlicki, ?ukasz,Nandan, Santosh R.,Coutinho, Evans C.
, (2017/10/06)
BM212 [1,5-diaryl-2-methyl-3-(4-methylpiperazin-1-yl)-methyl-pyrrole] is a pyrrole derivative with strong inhibitory activity against drug resistant Mycobacterium tuberculosis and mycobacteria residing in macrophages. However, it was not pursued because o
Aminomethylation of Imidazoheterocycles with Morpholine
Mondal, Susmita,Samanta, Sadhanendu,Singsardar, Mukta,Hajra, Alakananda
supporting information, p. 3751 - 3754 (2017/07/26)
A hitherto unreported aminomethylation occurs at C-3 of imidazopyridines with morpholine in the presence of (diacetoxyiodo)benzene at ambient temperature in short reaction times. This methodology is also applicable to indolizine, imidazo[2,1-b]thiazole, benzo[d]imidazo[2,1-b]thiazole, and indole. Interestingly, the aminomethylation involving morpholine as a source of methylene group is a new phenomenon. This protocol is of much potential for the synthesis of aminomethylated derivatives under mild reaction conditions.
Oxidative Cross-Coupling of sp3- and sp2-Hybridized C-H Bonds: Vanadium-Catalyzed Aminomethylation of Imidazo[1,2-a]pyridines
Kaswan, Pinku,Porter, Ashley,Pericherla, Kasiviswanadharaju,Simone, Marissa,Peters, Sean,Kumar, Anil,Deboef, Brenton
, p. 5208 - 5211 (2015/11/18)
The vanadium-catalyzed oxidative coupling of substituted 2-arylimidiazo[1,2-a]pyridines to N-methylmorpholine oxide, which acts as both a coupling partner and an oxidant, has been achieved. This reaction was applied to various substituted imidiazo[1,2-a]pyridine and indole substrates, resulting in yields as high as 90%. Mechanistic investigations indicate that the reaction may proceed via a Mannich-type process. This work demonstrates how oxidative aminomethylation can be used as a useful method to introduce tertiary amines into heterocycles, thus providing an alternative method for conventional Mannich-type reactions.
