1268167-76-5Relevant articles and documents
Highly Efficient and Practical Thiocyanation of Imidazopyridines Using an N-Chlorosuccinimide/NaSCN Combination
Zhang, Hailei,Wei, Qian,Wei, Shiqiang,Qu, Jingping,Wang, Baomin
, p. 3373 - 3379 (2016)
A direct C–H thiocyanation of imidazo[1,2-a]pyridines, and a practical sequential one-pot condensation/C–H thiocyanation process, using a combination of N-chlorosuccinimide/NaSCN for the synthesis of 3-thiocyanatoimidazo[1,2-a]pyridines have been develope
A multi pathway coupled domino strategy: I2/ TBHP-promoted synthesis of imidazopyridines and thiazoles via sp3, sp2 and sp C-H functionalization
Feng, Lei,Li, Shichen,Ma, Chen,Wang, Xinfeng,Wang, Yishou,Yao, Yiming
, p. 5919 - 5927 (2022/03/31)
I2/TBHP-promoted, one-pot, multi pathway synthesis of imidazopyridines and thiazoles has been achieved through readily available ethylarenes, ethylenearenes and ethynearenes. I2/TBHP as an initiator and oxidant is used to realize the C-H functionalization of this domino reaction. Simple and available starting materials, wide range of functional group tolerance, high potential for drug activity of the products and application in production are the advantageous features of this method.
Oxidation Potential-Guided Electrochemical Radical-Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines
Kim, Wansoo,Kim, Hun Young,Oh, Kyungsoo
, p. 15973 - 15991 (2021/07/26)
Oxidation potential-guided electrochemical radical-radical cross-coupling reactions between N-heteroarenes and sodium sulfinates have been established. Thus, simple cyclic voltammetry measurement of substrates predicts the likelihood of successful radical-radical coupling reactions, allowing the simple and direct synthetic access to 3-sulfonylated imidazopyridines and indolizines. The developed electrochemical radical-radical cross-coupling reactions to sulfonylated N-heteroarenes boast the green synthetic nature of the reactions that are oxidant- and metal-free.
One-pot NBS-promoted synthesis of imidazoles and thiazoles from ethylarenes in water
Chen, Liang,Zhu, Huajian,Wang, Jiang,Liu, Hong
, (2019/03/19)
A facile and eco-friendly method has been developed for the synthesis of imidazoles and thiazoles from ethylarenes in water. The reaction proceeds via in situ formation of α-bromoketone using NBS as a bromine source as well as an oxidant, followed by trapping with suitable nucleophiles to provide the corresponding products in good yields under metal-free conditions.
Straightforward synthesis of various 2,3-diarylimidazo[1,2-a]pyridines in peg400 medium through one-pot condensation and C-H arylation
Hiebel, Marie-Aude,Fall, Yacoub,Scherrmann, Marie-Christine,Berteina-Raboin, Sabine
, p. 4643 - 4650 (2014/08/05)
PEG400 is described herein as a suitable medium for the condensation of various 2-amino pyridines with α-bromo ketones. 2-Arylimidazo[1,2-a]pyridines were synthetized in a short time through microwave irradiation in moderate to excellent yields
Non-classical donor-acceptor-donor chromophores. A strategy for high two-photon brightness
Ciuciu, Adina I.,Firmansyah, Dikhi,Hugues, Vincent,Blanchard-Desce, Mireille,Gryko, Daniel T.,Flamigni, Lucia
, p. 4552 - 4565 (2014/06/09)
Rod-like π-expanded bis-imidazo[1,2-a]pyridines were designed and synthesized. Strategic placement of a central electron-poor unit at position C3 of the imidazo[1,2-a]pyridine core resulted in donor-acceptor-donor quadrupolar systems. We further demonstrated the applicability of the Ortoleva-King- Chichibabin tandem process in the preparation of complex imidazo[1,2-a] pyridines. The monomer model heterocycles, differing by substitution at C2 and C3, displayed luminescence properties marginally dependent on the substitution pattern and conjugation extension. The highest luminescence quantum yield (φflca. 0.2) is shown by the model compounds without a substitution at C3, whereas lower values are measured for the others. Quantum yields in toluene for the quadrupolar systems varied from φfl = 0.7 to φfl > 0.9. Apart from bis-imidazo[1,2-a]pyridine possessing two methyl groups, with φfl = 0.69 in toluene and 0.35 in dichloromethane, the luminescence properties were only slightly affected by the change in the solvent. Most of the fluorescence lifetimes ranged from 1-2 ns and the radiative rate constants reached values of ca. 6 × 108 s-1. Intense phosphorescence spectra at 77 K with lifetimes in the second range (τ = 0.6-1.3 s) are recorded for the monomers, whereas for the bis-imidazo[1,2-a]pyridines, phosphorescence spectra are detected only after enhancing intersystem crossing by heavy atoms. Non-linear optical properties of bis-imidazo[1,2-a]pyridines revealed two-photon absorption cross-sections (σ2) typically of the order of 500-800 GM. The remarkable fluorescence quantum yield, in combination with high a two-photon absorption cross-section, generated a two-photon brightness of ～500 to 750 GM units within the biological window (700-800 nm).
Copper-mediated trifluoromethylation of heteroaromatic compounds by trifluoromethyl sulfonium salts
Zhang, Cheng-Pan,Wang, Zong-Ling,Chen, Qing-Yun,Zhang, Chun-Tao,Gu, Yu-Cheng,Xiao, Ji-Chang
supporting information; experimental part, p. 1896 - 1900 (2011/04/16)
Copper is king! A convenient method for the synthesis of trifluoromethylated heteroaromatic compounds under mild conditions has been developed based on the observation that 1 can be reduced by certain metals (see scheme). Substrate 1 is assumed to be reduced by copper via a single-electron transfer mechanism, and CuCF3 is the most probable intermediate in this reaction. DMF=N,N-dimethylformamide, Tf=triflate.
