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.
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.
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.
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%).
