- Divergent Synthesis of Quinolones and Dihydroepindolidiones via Cu(I)-Catalyzed Cyclization of Anilines with Alkynes
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A unique and efficient method for one-pot synthesis of diverse 4-quinolones from simple and readily available primary anilines and alkynes via Cu(I)-catalyzed direct cyclization has been developed. The (thio)phenols were also found to visible substrates for this reaction. Moreover, an unprecedented synthesis of dihydroepindolidiones has been demonstrated by using secondary anilines as the versatile substrates.
- Xu, Xuefeng,Sun, Ruzhong,Zhang, Sheng,Zhang, Xu,Yi, Wei
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supporting information
p. 1893 - 1897
(2018/04/16)
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- Polyfunctional 4-quinolinones. Synthesis of 2-substituted 3-hydroxy-4-oxo-1,4-dihydroquinolines
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We present here two new methods based on rearrangement reactions to obtain novel 2-substituted 3-hydroxy-4-oxo-1,4-dihydroquinolines, an important family of heterocycles with potential applications. Alkyl 3-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylates were obtained by alkoxide promoted rearrangement of alkyl isatinacetates. A second synthetic route involves the alkoxide promoted reaction of both isatin and N-methylisatin, with alkylating agents having acidic methylenes. This reaction leads to the formation of spiroepoxyoxindoles via Darzens' condensation. When phenacyl bromides are used, the initially obtained benzoyl substituted spiroepoxyoxindoles were smoothly transformed into the corresponding 2-benzoyl-3-hydroxy-4-quinolinones with good to excellent yields.
- Shmidt, María S.,Perillo, Isabel A.,Camelli, Alicia,Fernández, María A.,Blanco, María M.
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supporting information
p. 1022 - 1026
(2016/02/18)
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- Facile synthesis of 4-quinolone derivatives via one-pot cascade reaction under transition-metal-free conditions
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A practical and efficient strategy has been described for the preparation of 4-quinolone derivatives. Using commercially available diethyl acetylenedicarboxylate and aromatic amines as starting materials, the synthetic protocol has been achieved and affor
- Huang, Chao,Guo, Jia-Hui,Fu, Huang-Mei,Yuan, Ming-Long,Yang, Li-Juan
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p. 3777 - 3781
(2015/06/08)
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- Synthesis of perspicamide A and related diverse analogues: Their bioevaluation as potent antileishmanial agents
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The first protocol for the synthesis of perspicamide A and related diverse analogues has been developed from economical and readily available starting materials. Furthermore, a few synthesized analogues, 24a, 24b, 24c, 24d, and 24l, exhibited potent activ
- Pandey, Anand Kumar,Sharma, Rashmi,Shivahare, Rahul,Arora, Ashish,Rastogi, Neeraj,Gupta, Suman,Chauhan, Prem M. S.
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p. 1534 - 1546
(2013/04/10)
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- SYNTHETIC CONNECTIONS TO THE AROMATIC DIRECTED METALATION REACTION. A MODIFIED von NIEMENTOWSKI QUINOLINE SYNTHESIS FROM ANTHRANILAMIDES
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Anthranilamides 1, A = NR2 derived from benzamides by directed ortho metalationamination, are converted into the corresponding imines 4 which upon treatment with LDA lead to substituted 4-quinolones 5 thus providing a general new quinoline synthesis (Tabl
- Chong, R.J.,Siddiqui, M.A.,Snieckus, V.
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p. 5323 - 5326
(2007/10/02)
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- Process for preparing certain pyrano[3,2-g]quinoline 2,8-dicarboxylates and 4-oxo-quinoline-2-carboxylates
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There is described a process for the production of a 1,4-dihydro-4-oxo-quinoline-2-carboxylic acid, or a salt, ester or amide thereof, which comprises cyclization of a corresponding 2-aminobenzoyl pyruvic acid or an ester thereof, and if desired or necess
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