- Synthesis of [1,4]Thiazino[4,3- a]indol-10-one Derivatives through Radical Anti Aza-Michael Addition of 2′-Aminochalcones
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An efficient method for the synthesis of [1,4]thiazino[4,3-a]indole derivatives using sodium chlorodifluoroacetate (ClCF2CO2Na) and elemental sulfur as the difluoromethylthiolating reagent system has been developed. Three-component reactions of 2′-aminochalcones, sulfur, and ClCF2CO2Na under basic conditions using TEMPO as the oxidant afforded [1,4]thiazino[4,3-a]indol-10-ones containing a difluoromethyl thioether moiety in good yields. Four bonds including one C-N, two C-S, and one C-C bonds are selectively formed in the sequential transformation process.
- Zhang, Pingshun,Yang, Linjie,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
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supporting information
p. 6094 - 6098
(2021/08/01)
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- 2-aryl-2,3-dihydro-4(1H)-quinolinone semicarbazone compound and application thereof
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The invention relates to the field of medicine technology, and a series of novel 2-aryl-2,3-dihydrogen-4(1H)-quinolinone semicarbazone derivatives (I) and pharmaceutically acceptable salts, solvates,optical isomers or polymorphs are designed and synthesized. The derivative (I) and its pharmaceutically acceptable salt, solvate, optical isomer or polymorph can be mixed as an active ingredient witha pharmaceutically acceptable carrier to prepare a pharmaceutical composition. A double dilution method is used for test of the antifungal activity of the derivative (I) and its pharmaceutically acceptable salt, solvate, optical isomer or polymorph, and the results show that the derivative has stronger killing effect on clinically common pathogenic fungi, and is expected to overcome the defects oflarge toxic and side effects, easy generation of drug resistance of azole antifungal medicines which are widely used clinically. The specific formula is shown in the description.
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Paragraph 0066; 0067; 0068
(2018/10/19)
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- Aza analogs of flavones as potential antimicrobial agents
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In search for the new antimicrobial agents owing to drug resistant bacteria and fungi, a series of rationally designed aza analogs of flavones has been designed and synthesized. The design of the analogs involved incorporation of quinolone nucleus within
- Sharma, Sahil,Thakur, Vikas,Ojha, Ritu,Budhiraja, Abhishek,Nepali, Kunal,Singh Bedi, Preet Mohinder
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p. 327 - 334
(2013/07/26)
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- Mild palladium-catalyzed oxidative direct ortho-C-H acylation of anilides under aqueous conditions
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Palladium-catalyzed cross-dehydrogenative coupling between anilides and aromatic aldehydes was achieved under aqueous conditions. A wide variety of the desired benzophenone derivatives was isolated in good to excellent yield. The reaction rate acceleration effect of acid and detergent has been demonstrated. Mechanistic insight has been obtained from quantum chemical calculations. Copyright
- Szabo, Fruzsina,Daru, Janos,Simko, Daniel,Nagy, Tibor Zs.,Stirling, Andras,Novak, Zoltan
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p. 685 - 691
(2013/04/10)
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- Palladium-catalyzed heteroannulation with acetylenic carbinols as synthons-synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones
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o-Iodoanilides 4 reacted with terminal acetylenic carbinols 5 under palladium-catalyzed conditions to yield o-substituted anilides 6. Most of the anilides 6 could be cyclized with NaOEt/EtOH to 2-arylquinolines 2. o-Iodoanilines 7 reacted with carbinols 5 leading to 8 which on palladium(II) assisted cyclisation afforded substituted quinolines 2. An excellent synthesis of the alkaloid dubamine (2n) is reported. Also, the anilides 6 on acid-catalyzed rearrangement, deprotection and cyclisation led to the 2-aryl-2, 3-dihydro-4(1H)-quinolones 16.
- Mahanty, Jyan S.,De, Mahuya,Das, Palas,Kundu, Nitya G.
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p. 13397 - 13418
(2007/10/03)
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- 2'-Substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis
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A series of 2'-substituted chalcone derivatives has been found to show potent inhibition of the production of IL-1β from human peripheral blood monocytes stimulated with lipopolysaccharide (LPS), with IC50 values in the 0.2-5.0-μM range. Some members of the series have also shown inhibition of septic shock induced in mice by injection of LPS, although with low potency. Qualitative structure-activity relationships have shown that the enone is required for activity, which may be mediated by conjugate addition of a biological nucleophile to the chalcone. Electron-poor aromatic rings β to the ketone give enhanced potency. Although electronic effects in the other ring (directly attached to the ketone) are minimal, this ring must possess an ortho substituent for good activity without cytotoxicity, suggesting a degree of selectivity which would not be expected for simple, nonspecific alkylating agents.
- Batt,Goodman,Jones,Kerr,Mantegna,McAllister,Newton,Nurnberg,Welch,Covington
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p. 1434 - 1442
(2007/10/02)
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- Synthesis of Quinolines and 2,3-Dihydro-4(1H)-quinolones. Palladium Catalysed Reaction of o-Iodoanilides with Acetylenic Carbinols
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A facile and general synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones was accomplished through palladium catalysed reaction of o-iodoanilides with acetylenic carbinols.Key Words: quinolines; 2,3-dihydro-4(1H)-quinolones; palladium catalysis; o-iodoanilines; acetylenic carbinols.
- Kundu, Nitya G.,Mahanty, Jyan S.,Das, Palas,Das, Biswajit
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p. 1625 - 1628
(2007/10/02)
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- The Chemistry of 2'-Amino Analogues of 2'-Hydroxychalcone and Its Derivatives
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The cyclization of 2'-aminochalcone (2a) and its side-chain additives has been studied for the development of syntheses of 2-aryl-4-quinolones. 2a and its 2'-acetamido 2b and 2'-benzenesulfonamido 2c derivatives underwent acid- or base-catalyzed cyclization to 1,2,3,4-tetrahydro-4-quinolones.The α,β-dibromides of 2b and 2c cyclized to cis-3-bromo-4-quinolones as did the corresponding α-bromochalcones and the α-bromo-β-methoxy additive of 2c. 2'-Acetamido-α-bromochalcone was cyclized by acid to 1,4-dihydro-2-phenyl-4-quinolone. 2'-Aminochalcone formed a stableepoxide which, with acid, gave cis-3-hydroxy-1,2,3,4-tetrahydro-3-phenyl-4-quinolone. 2'-Aminochalcones 2a-c and their additives, such as dibromide and epoxide, are useful, readily available precursors of various 2-aryl-4-quinolones.
- Donnelly, John A.,Farrell, David F.
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p. 1757 - 1761
(2007/10/02)
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