- Palladium catalyzed divergent cycloadditions of vinylidenecyclopropane-diesters with methyleneindolinones enabled by zwitterionic π-propargyl palladium species
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A palladium-catalyzed divergent synthesis of spirooxindoles fused with a five- or a six-membered ring by a cycloaddition reaction of vinylidenecyclopropane-diesters with methyleneindolinones was disclosed. This protocol features anin situgenerated unprecedented zwitterionic π-propargyl palladium species in cycloaddition reactions and a switchable process between (3+2) and (4+2) cycloadditions by changing the phosphine ligand.
- Niu, Ben,Wei, Yin,Shi, Min
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supporting information
p. 4783 - 4786
(2021/05/25)
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- Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones
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The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.
- Wang, Rong-Hui,Li, Ya-Ling,He, Hong-Jiao,Xiao, You-Cai,Chen, Fen-Er
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supporting information
p. 4302 - 4306
(2021/02/16)
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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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p. 1022 - 1026
(2016/02/18)
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- Reaction of isatin with alkylating agents with acidic methylenes
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The reaction of isatin (1) with different alkyl halides 2 and alkaline carbonates in aprotic polar solvents leads mainly to N-alkyl derivatives 3. The use of alkylating agents that have acidic methylenes leads to competitive formation of the corresponding epoxide 5. The formation of 5 is favored by low-polarity solvents at low temperatures and strong bases. Epoxides 5c, d obtained using NaEtOH/EtOH at 0-5 °C are transformed into the corresponding 4-quinolinones 6 at higher temperatures. The use of Ag2CO3 allows obtaining compounds 3 as major products, along with varying amounts of labile O-alkyl derivatives 4 and dimerization products.
- Shmidt, María S.,Perillo, Isabel A.,González, Mercedes,Blanco, María M.
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supporting information; experimental part
p. 2514 - 2517
(2012/06/18)
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- USE OF SPIRO-OXINDOLE COMPOUNDS AS THERAPEUTIC AGENTS
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This invention is directed to methods of using spiro-oxindole compounds of formula (I): wherein k, j, Q, R1, R2a, R2b, R2c, R2d, R3a, R3b, R3c, and R3d are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, for the treatment and/or prevention of hypercholesterolemia, benign prostatic hyperplasia, pruritis and cancer.
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- Activation of the NC-H bond of Morita-Baylis-Hillman adducts of N-substituted isatins with cerium ammonium nitrate (CAN) and alcohol (ROH)
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A study on the activation of the NC-H bond of Morita-Baylis-Hillman adducts of N-substituted isatin with cerium ammonium nitrate (CAN) and saturated and unsaturated alcohols have been carried out. The choice of a Morita-Baylis- Hillman adduct for this stu
- Shanmugam, Ponnusamy,Vaithiyanathan, Vadivel
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experimental part
p. 591 - 599
(2009/10/17)
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- OXINDOLE COMPOUNDS AND THEIR USES AS THERAPEUTIC AGENTS
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This invention is directed to oxindole compounds that are useful for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain. Pharmaceutical compositions comprising the compounds and methods of using the compounds are also disclosed.
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Page/Page column 81
(2010/11/24)
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- A convenient methodology for the N-alkylation of isatin compounds
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A simple, high yielding, methodology for the N-alkylation of substituted isatin derivatives using calcium hydride in DMF is detailed.
- Garden, Simon J.,Torres, Jose C.,Da Silva, Leonardo E.,Pinto, Angelo C.
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p. 1679 - 1689
(2007/10/03)
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