22059-64-9Relevant academic research and scientific papers
Green Approach for Visible-Light-Induced Direct Functionalization of 2-Methylquinolines
Dantas, Juliana A.,Echemendía, Radell,Santos, Marilia S.,Paix?o, Márcio W.,Ferreira, Marco Antonio B.,Corrêa, Arlene G.
, p. 11663 - 11678 (2020)
A transition metal-and oxidant-free visible light-photoinduced protocol for direct functionalization of 2-methylquinolines has been developed. This protocol enabled the C-H functionalization of substituted 2-methylquinolines with diacetyl or ethyl pyruvate, under environmentally friendly conditions. A mechanistic investigation based on density functional theory (DFT) calculations provided details about the origins of reactivity and selectivity.
The structure elucidation of mequindox and 1,4-bisdesoxymequindox: NMR analyses, FT-IR spectra, DFT calculations and thermochemical studies
Zhang, Jiaheng,He, Xin,Gao, Haixiang
, p. 109 - 115 (2011)
In the current work, we report a combined experimental and theoretical study on the molecular conformation, vibrational spectra, and nuclear magnetic resonance (NMR) spectra of mequindox (MEQ) and 1,4-bisdesoxymequindox (1,4-BDM). The geometric structure and vibrational frequencies of MEQ and 1,4-BDM have been calculated by density functional theory employing the B3LYP functional and 6-311++G(d,p) basis set. The 1H and 13C NMR chemical shifts have been calculated by gauge-including atomic orbital method with B3LYP 6-311++G(2df,2pd) approach. The calculation results have been applied to simulate the infrared and NMR spectra of the compounds. The theoretical results agree well with the observed spectra. The bond dissociation enthalpy of MEQ and the heat of formation of MEQ and 1,4-BDM have also been computed.
SYNTHESIS AND PROPERTIES OF HETEROCYCLIC ANALOGS OF 4-AZIDOCHALCONE
Budyka, M. F.,Kantor, M. M.,Alfimov, M. V.
, p. 1072 - 1075 (1991)
A study has been made of the spectral and photochemical properties of a series of heterocyclic analogs of 4-azidochalcone, specifically the pyridine, quinoline, isoquinoline, and quinoxaline derivatives.It has been shown that the absorption spectra of most of the 4-azidocinnamoylarenes are shifted bathochromically in comparison with 4-azidochalcone.The quantum yields of photodissociation of the compounds that were investigated were found to vary within the limits 0.70 +/- 0.15.With steric hindrance for the planar conformation of the molecule, a hypsochromic shift ofthe absorption spectra is observed, along with a slight decrease of the quantum yield.
Quinoline-Fused Lactones via Tandem Oxidation Cyclization: Metal-Free sp3C-H Functionalization
Garia, Alankrita,Chauhan, Parul,Halder, Riya,Jain, Nidhi
, p. 538 - 546 (2021)
A unique lactonization of 2-methyl-3-acyl-4-phenylquinolines using PhIO as the oxidant and selectfluor as an additive is reported. The reaction occurs under ambient conditions through tandem oxidation and cyclization of sp3 C-H bonds under metal-free conditions. The heterocycle-fused lactones are obtained in moderate to good yield.
Method for synthesizing quinoxaline compounds through double-protein catalytic cascade reaction
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Paragraph 0076-0082, (2021/01/25)
The invention relates to the technical field of biological catalytic synthesis and particularly discloses a method for synthesizing quinoxaline compounds by a double-protein catalytic cascade reaction. The method comprises the steps as follows: a beta-keto ester compound, substituted o-phenylenediamine and methylphenylsulfonyl azido are taken as reactants to be dissolved in a solvent, a catalyst and a surfactant are added, the mixture is stirred to react to produce a product, and the product is sequentially dried, concentrated and purified, wherein the solvent is water, and the catalyst is procine pancreaslipase (PPL) and hemoglobin from bovine blood (HbBv). The process is convenient, a heme protein catalytic carbene reaction and a lipase protein catalytic reaction are coupled to constructa green method for synthesizing quinoxaline compound by double proteins by a one-pot method, the target product can be rapidly and conveniently synthesized, meanwhile, synthesis is completed in water, and the problems that the existing quinoxaline compound preparation method comprises more synthesis steps and is not green and environmentally friendly enough are solved.
A dual-protein cascade reaction for the regioselective synthesis of quinoxalines
Li, Fengxi,Li, Zhengqiang,Tang, Xuyong,Wang, Chunyu,Wang, Lei,Wang, Zhi,Xu, Yaning
supporting information, p. 3900 - 3904 (2020/06/08)
In this work, an efficient dual-protein (lipase and hemoglobin) system was successfully constructed for the regioselective synthesis of quinoxalines in water. A set of quinoxalines were obtained in high yields under optimal reaction conditions. This dual-protein method exhibited a regioselectivity higher than those of previously reported methods. This study not only provides a green and mild strategy for the synthesis of quinoxalines but also expands the application of lipase and hemoglobin in organic synthesis.
Iron-Catalyzed Minisci Type Acetylation of N-Heteroarenes Mediated by CH(OEt)3/TBHP
Srinivasulu,Shantharjun,Vani,Ashalu, K. Chinna,Mohd,Wencel-Delord,Colobert,Reddy, K. Rajender
supporting information, p. 1815 - 1819 (2019/02/20)
Iron-catalyzed acetylation of electron deficient N-heteroarenes has been reported using triethylorthoformate as robust and inexpensive acetyl source. This new method is successfully applied for the acetylation of quinolines, isoquinoline, quinoxalines, arylpyridines, bipyridines, and benzothiazole.
Iron-catalyzed Minisci acylation of N-heteroarenes with α-keto acids
Wang, Xiu-Zhi,Zeng, Cheng-Chu
supporting information, p. 1425 - 1430 (2019/02/01)
An efficient and mild protocol has been developed for the Minisci acylation reactions of nitrogen-containing heteroarenes with α-keto acids. Distinct from the conventional Minisci acylation conditions, the chemistry was performed using non-noble metal Fe(II), instead of expensive Ag(I) salt, as catalyst. A wide range of substrates, including aliphatic or aromatic α-keto acids, as well as various N-heteroarenes, proved to be compatible with the protocol. Scale-up experiment also demonstrates the practicality of the approach.
One-Pot Telescoped Synthesis of Thiazole Derivatives from β-Keto Esters and Thioureas Promoted by Tribromoisocyanuric Acid
De Andrade, Vitor S. C.,De Mattos, Marcio C. S.
, p. 4867 - 4874 (2018/12/13)
A simple and efficient one-pot protocol has been developed for the synthesis of thiazole derivatives from readily available starting materials. Tribromoisocyanuric acid was successfully used for α-monohalogenation of β-keto esters in aqueous medium, which
Isobutyl Nitrite-Mediated Synthesis of Quinoxalines through Double C?H Bond Amination of N-Aryl Enamines
Jiao, Yan-Xiao,Wei, Lin-Su,Zhao, Chun-Yang,Wei, Kai,Mo, Dong-Liang,Pan, Cheng-Xue,Su, Gui-Fa
supporting information, p. 4446 - 4451 (2018/10/20)
An efficient and metal-free double C?H bond amination of N-aryl enamines using isobutyl nitrite (IBN) has been developed. This method enables the preparation of functionalized quinoxalines in good to excellent yields and tolerates a variety of N-aryl enamines with diverse functional substituents. Mechanistic studies revealed the presence of a key β-imino oxime ester intermediate. A quinoxaline derivative could be prepared from β-carbonyl ester in one-pot sequence on a gram scale. Finally, two important quinoxaline scaffolds were easily prepared in moderate yields over two steps. (Figure presented.).
