- Synthesis method of imiquimod intermediate
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The invention discloses a synthesis method of an imiquimod intermediate, the synthesis method comprises the following steps: step 1, under the condition of a catalyst, heating quinoline and NBS in a solvent for reaction to obtain a compound 2; step 2, in the solvent, mixing the compound 2 with isobutylamine, adding a catalyst, and carrying out a heating reaction to obtain a compound 3; step 3, heating the compound 3 and NBS in the solvent for reaction to obtain a compound 4; step 4, in the first stage, the compound 4 and formamide are subjected to a heating reaction under the action of the catalyst; and in the second stage, hydrochloric acid is used for treatment to obtain a compound 1. Compared with the prior art, the method has the advantages of low price of initial raw materials, simple reaction operation in each step, high yield, less three wastes and high production efficiency.
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Paragraph 0009; 0024-0027; 0038-0041
(2021/10/02)
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- 3,6-DISUBSTITUTED-2-PYRIDINALDOXIME SCAFFOLDS
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The present invention relates to a compound of formula (I), or one of its pharmaceutically acceptable salts: wherein R1, R2 and -X-Y- have specific definitions. It also relates to the use of such a compound as reactivator of acetylcholinesterase for treating organophosphorous nerve agents poisoning; and to a process for preparing it.
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Paragraph 0095; 0132-0134
(2020/08/27)
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- Direct enantioselective vinylogous Mannich-type reactions of acyclic enals: New experimental insights into the E/Z-dilemma
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The direct heterofunctionalization of acyclic α,β-unsaturated aldehydes with N-acylquinolinium ions contemplating the formation of two stereocentres is studied using dienamine catalysis. This work gives some new experimental insights on the remote stereocontrol in dienamine catalysis using unbiased aliphatic systems and large electrophiles, pointing to a (Z)-preference of the reactive configuration of the second double bond.
- Vargiu, Michela,Favero, Lucilla,Menichetti, Andrea,Di Bussolo, Valeria,Marchetti, Fabio,Pescitelli, Gennaro,Di Pietro, Sebastiano,Pineschi, Mauro
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supporting information
p. 522 - 533
(2019/05/27)
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- A highly practical and convenient halogenation of fused heterocyclic N-oxides
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A novel, simple and practical method for the regioselective halogenation of fused heterocyclic N-oxides has been developed. It employs Vilsmeier reagent, generated in situ by POX3and DMF, as both the activating agent and the nucleophilic halide source. The method is amenable across a broad range of substrates, including quinolines, isoquinolines and the diazine N-oxides, possessing a variety of substitution patterns. Furthermore, all of the reagents associated are cheap and easy to obtain. The potential extension of this method to a one-pot oxidation/halogenation sequence that obviates the need for isolation of the N-oxide intermediates is also presented.
- Wang, Dong,Wang, Yuxi,Zhao, Junjie,Li, Linna,Miao, Longfei,Wang, Dong,Sun, Hua,Yu, Peng
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p. 5762 - 5768
(2016/08/30)
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- SUBSTITUTED ACETYLENE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR4
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The present invention relates to novel acetylene derivatives as positive allosteric modulators for modulating metabotropic glutamate receptor subtype 4 (mGluR4) and/or altering glutamate level or glutamatergic signalling.
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Page/Page column 51
(2014/08/20)
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- Full-color tunable photoluminescent ionic liquid crystals based on tripodal pyridinium, pyrimidinium, and quinolinium salts
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Color-tunable luminescent ionic liquid crystals have been designed as a new series of luminescent materials. To achieve tuning of emission colors, intramolecular charge transfer (ICT) character has been incorporated into tripodal molecules. A series of th
- Tanabe, Kana,Suzui, Yuko,Hasegawa, Miki,Kato, Takashi
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scheme or table
p. 5652 - 5661
(2012/06/04)
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- Application of fragment screening and merging to the discovery of inhibitors of the mycobacterium tuberculosis cytochrome P450 CYP121
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Pieces of the puzzle: The first fragment-based approach was used to target cytochrome P450 enzymes (CYPs) for drug development (see scheme). The experiments provide new insights into the binding site of the essential Mycobacterium tuberculosis CYP121 enzyme, and resulted in a promising novel lead compound based on fragment merging.
- Hudson, Sean A.,McLean, Kirsty J.,Surade, Sachin,Yang, Yong-Qing,Leys, David,Ciulli, Alessio,Munro, Andrew W.,Abell, Chris
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supporting information
p. 9311 - 9316
(2012/10/30)
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- Assembly of 4-aminoquinolines via palladium catalysis: A mild and convenient alternative to SNAr methodology
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4-Aminoquinolines, classically prepared via SNAr chemistry from an amine and 4-haloquinoline, are important scaffolds in medicinal chemistry. Interest in these compounds prompted us to explore palladium catalysis as an alternative to the existing methods for their preparation. Initial results followed by an iterative screening paradigm confirmed Pd(OAc)2/ DPEphos/K3PO4 as a mild and convenient alternative for the formation of the C-N bond in 4-aminoquinolines. A description of the screen and the scope of this methodology are discussed herein.
- Margolis, Brandon J.,Long, Kimberly A.,Laird, Dana L. T.,Ruble, J. Craig,Pulley, Shon R.
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p. 2232 - 2235
(2007/10/03)
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- Photochemical Reaction of Ethoxycarbonyl-Substituted Quinolines
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The photochemical reactions of the quinoline derivatives substituted by an ethoxycarbonyl group at the 2-, 3-, and 4-positions of a quinoline nucleus have been investigated in several alcohols and cyclohexane.Irradiation of ethyl 4-quinolinecarboxylate (1) yielded ethyl 2-hydroxyalkyl-4-quinolinecarboxylates (4a-c) in alcohols and ethyl 2-cyclohexyl-4-quinolinecarboxylate (4d) in cyclohexane in a good yield, respectively.The photochemical reactions of ethyl 3-quinolinecarboxylate (2) showed remarkable solvent dependency.Irradiation in methanol and cyclohexane afforded a solvent-additive product, ethyl 4-hydroxymethyl-1,4-dihydro-3-quinolinecarboxylate (5a) and ethyl 4-cyclohexyl-1,4-dihydro-3-quinolinecarboxylate (5b), while such photoaddition of the solvent did not proceed in ethanol and 2-propanol but instead ethyl 1,4-dihydro-3-quinolinecarboxylate (6) and dimeric compounds were formed, both of which were unstable and finally reverted to 2 at room temperature in air.In the case of ethyl 2-quinolinecarboxylate two types of the products, ethyl 4-hydroxyalkyl-1,4-dihydro-2-quinolinecarboxylate (7) and ethyl 1,4-dihydro-2-quinolinecarboxylate (8) were obtained in ethanol and 2-propanol but the yields of those products were poor.On the basis of triplet quenching experiments, the photochemical reactions of those ethyl quinolinecarboxylates are suggested to occur through hydrogen abstraction from the solvents by the ring nitrogen in the S1 state.
- Ono, Isao,Hata, Norisuke
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p. 2891 - 2898
(2007/10/02)
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