159679-68-2Relevant academic research and scientific papers
KIO4-mediated Selective Hydroxymethylation/Methylenation of Imidazo-Heteroarenes: A Greener Approach
Braga, Antonio Luiz,Franco, Marcelo Straesser,Rafique, Jamal,Saba, Sumbal
supporting information, p. 18454 - 18460 (2021/07/21)
Herein, we report a KIO4-mediated, sustainable and chemoselective approach for the one-pot C(sp2)?H bond hydroxymethylation or methylenation of imidazo-heteroarenes with formaldehyde, generated in situ via the oxidative cleavage of ethylene glycol or glycerol (renewable reagents) through the Malaprade reaction. In the presence of ethylene glycol, a series of 3-hydroxymethyl-imidazo-heteroarenes was obtained in good to excellent yields. These compounds are important intermediates to access pharmaceutical drugs, e.g., Zolpidem. Furthermore, by using glycerol, bis(imidazo[1,2-a]pyridin-3-yl)methane derivatives were selectively obtained in good to excellent yields.
Formation of Methylene Linkage for N-Heterocycles: Sequential C-H and C-O Bond Functionalization of Methanol with Cosolvent Water
Li, Na,Bai, Jinku,Zheng, Xiaolin,Rao, Honghua
, p. 6928 - 6939 (2019/06/14)
An iron-catalyzed methylene forming strategy is disclosed through sequential C-H and C-O bond functionalization of methanol with cosolvent water. This protocol provides an easy and novel access to methylene-tethered imidazo[1,2-a]pyridine and 2-aminopyridine analogues in a sustainable manner and represents a complementary approach to traditional methylene forming strategies.
Oxidative sulfonamidomethylation of imidazopyridines utilizing methanol as the main C1 source
Zhao, Xue-Mei,Huang, En-Ling,Zhu, Yu-Shen,Li, Jing,Song, Bing,Zhu, Xinju,Hao, Xin-Qi
supporting information, p. 4869 - 4878 (2019/05/24)
An efficient one pot, three component synthesis of C3 sulfonamidomethylated imidazopyridines has been disclosed under metal-free conditions, which utilized the commercially available and renewable reagent methanol as the main methylene source. A wide range of substituted imidazopyridines and sulfamides/amines were well tolerated to afford the corresponding products in up to 92% yield. In the isotopic labelling experiment, it was found that a minor part of the methylene also originated from DTBP. Moreover, the radical scavenger reactions were conducted, which suggested that a free-radical mechanism was probably not involved. The current methodology featured several advantages, including broad substrate scope, good functional group tolerance and high reaction efficiency.
I2O5-Mediated Iodocyclization Cascade of N-(1-Arylallyl)pyridine-2-amines with Concomitant C=C Bond Cleavage: A Synthesis of 3-Iodoimidazo[1,2- a]pyridines
Zhou, Bingwei,Yuan, Yuan,Jin, Hongwei,Liu, Yunkui
supporting information, p. 5773 - 5782 (2019/05/10)
A facile method for the synthesis of 3-iodoimidazo[1,2-a]pyridines has been successfully developed involving an I2O5-mediated iodocyclization cascade of N-(1-arylallyl)pyridin-2-amines with concomitant C=C bond cleavage. Preliminary mechanistic studies reveal that this protocol might undergo an oxidative cyclization/decarboxylation/iodination sequence in which I2O5 is used as both an oxidant and an iodine source. The present protocol has advantages of wide substrate scope, simple operation, and metal-free conditions.
Exploration of the CuAAC reaction for the synthesis of novel 3-(triazol-1-yl)methyl-imidazo[1,2-a]pyridines
Khedar, Poonam,Pericherla, Kasiviswanadharaju,Kumar, Anil
, p. 2609 - 2614,6 (2012/12/12)
The archetypical CuAAC click chemistry is explored to assemble diverse 3-(triazol-1-yl)methyl-imidazo[1,2-a]pyridines. The approach is simple, general, and environmentally benign to generate a library of novel triazolo-imidazo[1,2- a]pyridine derivatives in good yield (30-90%).
