613-19-4Relevant articles and documents
Synthesis method of 2-methyl-3-hydroxyquinoline and preparation method of quinotrione disperse dye
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Paragraph 0089-0134, (2020/12/30)
The invention relates to a synthesis method of 2-methyl-3-hydroxyquinoline and a preparation method of a quinotrione disperse dye. The synthesis method of the 2-methyl- 3-hydroxyquinoline comprises the steps of mixing o-aminobenzaldehyde, chloroacetone, a base catalyst, a phase transfer catalyst and a solvent, adjusting the pH value to 11 to 13, and fully contacting the raw materials under the action of the phase transfer catalyst to obtain a uniformly mixed homogeneous mixed solution with a specific pH value; and then carrying out micro-channel reaction on the mixed solution. In the micro-channel reaction process, reaction materials in the mixed solution is subjected to micron or millimeter-level micro contact reaction, the reaction speed and the reaction selectivity are improved, and theprobability of self-condensation polymerization of o-aminobenzaldehyde or chloroacetone in the micro-channel reaction process is reduced; and therefore, the yield of the 2-methyl-3-hydroxyquinoline is improved.
Multi-Functional Oxidase Activity of CYP102A1 (P450BM3) in the Oxidation of Quinolines and Tetrahydroquinolines
Li, Yushu,Wong, Luet L.
, p. 9551 - 9555 (2019/08/06)
Tetrahydroquinoline, quinoline, and dihydroquinolinone are common core motifs in drug molecules. Screening of a 48-variant library of the cytochrome P450 enzyme CYP102A1 (P450BM3), followed by targeted mutagenesis based on mutation-selectivity correlations from initial hits, has enabled the hydroxylation of substituted tetrahydroquinolines, quinolines, and 3,4-dihydro-2-quinolinones at most positions around the two rings in good to high yields at synthetically relevant scales (1.5 g L?1 day?1). Other oxidase activities, such as C?C bond desaturation, aromatization, and C?C bond formation, were also observed. The enzyme variants, with mutations at the key active site residues S72, A82, F87, I263, E267, A328, and A330, provide direct and sustainable routes to oxy-functionalized derivatives of these building block molecules for synthesis and drug discovery.
Simple synthesis of 3-hydroxyquinolines via Na2S2O4-mediated reductive cyclization of (2-(2-nitrophenyl)oxiran-1-yl)(aryl)methanones (o-nitrobenzalacetophenone oxides)
Mamedov, Vakhid A.,Mamedova, Vera L.,Syakaev, Victor V.,Korshin, Dmitry E.,Khikmatova, Gul'naz Z.,Mironova, Ekaterina V.,Bazanova, Olga B.,Rizvanov, Il'dar Kh.,Latypov, Shamil K.
, p. 5082 - 5090 (2017/07/28)
An efficient sodium dithionite (Na2S2O4)-mediated method for construction of 3-hydroxyquinolines via in situ Meinwald rearrangement/intramolecular reductive cyclization of o-nitrobenzalacetophenone oxides has been developed. The practical approach is of excellent functional group compatibility with as high as 98% yield under mild reaction conditions. Moreover, further manipulation successfully furnished 4-bromo substituted derivatives which may provide a promising potential application in exploring biologically active analogs of 3-hydroxyquinolines.
