214610-10-3Relevant articles and documents
Oxoarylation of ynamides with N-aryl hydroxamic acids
Chen, Changwei,Zhang, Hongyu,Xu, Gang,Cui, Sunliang
, p. 2551 - 2554 (2021)
Ynamides are electron-rich alkynes with unique reactivities and act as flexible building blocks in organic synthesis. Therefore, the investigation for transformation of ynamides with exceptional selectivity and efficiency is attractive and interesting. He
Desymmetrization of Prochiral Cyclopentenes Enabled by Enantioselective Palladium-Catalyzed Oxidative Heck Reaction
Chen, Guihua,Cao, Jian,Wang, Qian,Zhu, Jieping
, p. 322 - 325 (2020)
In the presence of a catalytic amount of Pd(TFA)2 and a chiral Pyox ligand under oxygen atmosphere, oxidative Heck reaction between arylboronic acids and 4-substituted or 4,4-disubstituted cyclopent-1-enes afforded the chiral arylated products with concurrent creation of two stereocenters in good yields with excellent diastereo- and enantioselectivities.
Highly Stereoselective [4+2] and [3+2] Spiroannulations of 2-(2-Oxoindolin-3-ylidene)acetic Esters Catalyzed by Bifunctional Thioureas
Monari, Magda,Montroni, Elisa,Nitti, Andrea,Lombardo, Marco,Trombini, Claudio,Quintavalla, Arianna
, p. 11038 - 11049 (2015)
A new Michael-Michael cascade reaction between 2-(2-oxoindolin-3-ylidene)acetic esters 1 and nitroenoates 2, catalyzed by bifunctional thioureas, is investigated. The combination of the two Michael reactions results in a novel and facile [4+2] or [3+2] spiroannulation process, which is characterized by the following features: 1) two carbon-carbon bonds and four stereocenters, including a quaternary spiro carbon, are formed under mild conditions; 2) an unprecedented and stereochemically defined substitution pattern on the spirocarbocyclic unit is obtained; 3) the double-bond configuration of the donor-acceptor nitroenoate 2 determines the absolute configuration of the spiro center, whereas the remaining stereocenters are formed under control of the catalyst. The effect on the final stereochemical outcome of structural variations of each starting material, catalyst, and experimental conditions is analyzed in detail. In particular, the use of specifically designed chiral nitroenoates enables diverse polyfunctional spirocyclohexane derivatives containing six consecutive stereogenic centers to be constructed. To our knowledge, this is the first asymmetric organocatalytic strategy enabling both five- and six-membered β-nitro spirocarbocyclic oxindoles.
Conversion of 1-Boc-indoles to 1-Boc-oxindoles
Vazquez, Enrique,Payack, Joseph F.
, p. 6549 - 6550 (2004)
A facile synthesis of substituted oxindoles 2 from the corresponding indole is described. The reaction, which proceeds through the 2-(indolyl) borate intermediate, is general and applicable to several indoles.
Studies on protection of oxindoles
Rajeswaran, Walajapet G.,Cohen, Louis A.
, p. 11375 - 11380 (1998)
Protection of amide nitrogen of oxindole and methyloxindole using Boc and Z-groups has been described. Sodium carbonate was found to be an effective base for these protections.
A Unified Catalytic Asymmetric (4+1) and (5+1) Annulation Strategy to Access Chiral Spirooxindole-Fused Oxacycles
Gao, Min,Gong, Xiangnan,Hu, Lin,Luo, Yanshu,Xia, Yuanzhi,Xu, Qianlan,Zhao, Yukun
supporting information, p. 19813 - 19820 (2021/08/03)
A unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides has been achieved in the presence of a chiral phase-transfer catalyst (PTC). This general strategy utilizes peroxides as unique bielectrophilic four- or five-atom synthons to participate in the C?C and the subsequent umpolung C?O bond-forming reactions with one-carbon unit nucleophiles, thus providing a distinct method to access the valuable chiral spirooxindole-tetrahydrofurans and -tetrahydropyrans with good yields and high enantioselectivities under mild conditions. DFT calculations were performed to rationalize the origin of high enantioselectivity. The gram-scale syntheses and synthetic utility of the resultant products were also demonstrated.
NOVEL COMPOUNDS USEFUL AS POLY(ADP-RIBOSE) POLYMERASE (PARP) INHIBITORS
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Paragraph 214, (2021/11/06)
The present invention provides novel poly(ADP-ribose) polymerase (PARP) inhibitors, methods of preparing them, pharmaceutical compositions containing them and methods for the treatment, prevention and/or amelioration of PARP mediated diseases or disorders using them. In particular, the compounds described herein are useful for the treatment of carcinoma of the breast, ovarian cancer, carcinoma of the liver, carcinoma of the lung, small cell lung cancer, esophageal cancer, gall bladder cancer, pancreatic cancer and stomach cancer.
TMSOTf-mediated approach to 1,3-oxazin-2-one skeleton through one-pot successive reduction-[4 + 2] cyclization process of imides with ynamides
Zhang, Chen-Chen,Huo, Zhi-Peng,Tang, Mei-Lin,Liang, Yong-Xi,Sun, Xun
supporting information, (2021/03/15)
A one-pot approach to access functionalized 1,3-oxazin-2-one skeleton has been developed through successive reduction and subsequent [4 + 2] cyclization process of N-Boc lactams with ynamides by TMSOTf. As a result, a number of five to seven membered ring fused bicyclic [1,2-c][1,3]oxazin-1-ones 12a-m and tricyclic derivatives 13a-f were obtained in moderate to excellent yields with excellent regioselectivities. Moreover, linear N-Boc amides 9a-e were also amenable to this transformation, and the desired 3,4-dihydro-1,3-oxazin-2-ones 14a-m were readily achieved in moderate yields with excellent regioselectivities.
LACTAM COMPOUND AS FXR RECEPTOR AGONIST
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Paragraph 0168, (2020/04/21)
Disclosed is a compound as shown in formula (I), an optical isomer thereof or a pharmaceutically acceptable salt thereof, and the present invention relates to the use of same in the preparation of a drug for treating FXR-related diseases.
Manganese-Catalyzed Asymmetric Oxidation of Methylene C-H of Spirocyclic Oxindoles and Dihydroquinolinones with Hydrogen Peroxide
Qiu, Bin,Xu, Daqian,Sun, Qiangsheng,Lin, Jin,Sun, Wei
supporting information, p. 618 - 622 (2019/01/21)
A highly efficient strategy for the enantioselective oxidation of methylene C-H of spirocyclic oxindoles and dihydroquinolinones has been established, in which an earth-abundant manganese catalyst and hydrogen peroxide are used. Noteworthy, the manganese catalyst can be applied to the asymmetric hydroxylation of spirocyclic 2,3-dihydroquinolin-4-ones with 94-99% ee.
