92552-73-3Relevant academic research and scientific papers
Organocatalytic Enantioselective Synthesis of Tetrahydro-Furanyl Spirooxindoles via [3+2] Annulations of 3-Hydroxyoxindoles and Cyclic Ketolactams
Liu, Yue,Zhang, Ying,Huang, Qian-Wei,Gou, Chuan,Li, Qing-Zhu,Dai, Qing-Song,Leng, Hai-Jun,Li, Jun-Long
, p. 2177 - 2182 (2021/03/08)
Asymmetric construction of pharmacologically interesting tetrahydrofuranyl spirooxindole frameworks has been achieved through organocatalytic [3+2] annulations of the readily available 3-hydroxyoxindoles and pyrrolidone-derived cyclic ketolactams. A variety of chiral spiro tetrahydrofuranyl products, which contain four contiguous stereocenters including two tetrasubstituted carbon centers, have been rapidly synthesized with remarkable results (up to 99% yield, >95:5 dr, and 99:1 er). Synthetic derivatization of the hemiketal moiety enables the installation of various halogen atoms into the structurally complex molecules in a stereospecific manner. Preliminary screening of anticancer bioactivity was performed, and 4 w showed obvious inhibitory capacity to the proliferation on a panel of cancer cell lines. (Figure presented.).
Oxindole spiro-tetrahydrofuran compound as well as preparation method and application thereof
-
, (2020/04/29)
The invention provides an indole tetrahydrofuran oxide compound or a crystal form thereof, wherein the indole tetrahydrofuran oxide compound is as shown in a formula (I). R1 is selected from benzene rings, naphthalene rings and thiophene rings or cinnamyl, R2 is selected from H, F, Cl, Br and I or C1-3 alkoxy, R3 is selected from H and benzyl or C1-C3 alkyl, and R4 is H, F, Cl, Br, I and C1-3 alkoxy or C1-C3 alkyl. The invention further provides a method for preparing the compound. The compound is simple and convenient in preparation method, moderate in reaction and high in yield and has anti-tumor activity and a wide market application prospect.
3-Hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one as a versatile intermediate for retro-Henry and Friedel-Crafts alkylation reactions in aqueous medium
Nagaraju, Sakkani,Sathish, Kota,Paplal, Banoth,Satyanarayana, Neeli,Kashinath, Dhurke
, p. 14045 - 14050 (2019/09/18)
The first example of a retro-Henry type reaction is reported using 3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-ones which are prepared via catalyst-free Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin. These compounds were used
Domino Grignard Addition and Oxidation for the One-Pot Synthesis of C2-Quaternary 2-Hydroxyindoxyls
Mandal, Tirtha,Chakraborti, Gargi,Maiti, Subhadip,Dash, Jyotirmayee
supporting information, p. 8044 - 8048 (2019/10/11)
We herein delineate an unexplored reactivity of 3-hydroxyoxindoles toward Grignard addition enabling a rapid access to a broad range of unnatural C2-quaternary 2-hydroxyindoxyls in high yields. The reaction proceeds via a mechanistically intriguing one-pot 1,2-hydride shift followed by autoxidation pathway. The utility of this method is demonstrated by the synthesis of a new class of bis-indoxyl spirofuran derivatives.
Oxoindole spiral tetrahydrofuran framework and its crystal and preparation method
-
, (2018/08/04)
The invention discloses an oxoindole spiral tetrahydrofuran framework and its preparation method. The structural formula is shown as Formula I. The invention further discloses a crystal form of the compound shown in Formula I; the crystal form is a monoclinic system, the cell parameter alpha is equal to 90 degrees, beta is equal to 94.278(3) degrees, and gamma is equal to 90 degrees; the space group is P21, Z=2; the cell volume is shown as specification. The invention further discloses a preparation method of the crystal form, and also discloses an application of the compound, or its crystal form, or its solvent compound, or pharmaceutically acceptable salts in preparation of anti-cancer drugs.
Oxoindolespiro tetrahydrofuran fluoride, crystal, preparation method and application thereof
-
, (2018/09/12)
The invention discloses oxoindolespiro tetrahydrofuran fluoride and a preparation method thereof. The structural formula of oxoindolespiro tetrahydrofuran fluoride is shown as formula I. The inventionfurther discloses a crystal form of a compound shown as the formula I, the crystal form is a monoclinic system, cell parameters include that a=9.09964(19) angstrom, b=9.3177(3) angstrom, c=15.6040(4)angstrom, alpha is equal to 90 degrees, beta is equal to 99.228 (2) degrees, and gamma is equal to 90 degrees; space group is P21, Z=2, and cell volume is 1305.91(6) angstrom. The invention further discloses a preparation method of the crystal form, the compound or the crystal form thereof or a solvate thereof or application of pharmaceutically acceptable salt thereof in preparing antitumor drug.
Iridium-Catalyzed Enantioselective and Diastereoselective Allylation of Dioxindoles: A One-Step Synthesis of 3-Allyl-3-hydroxyoxindoles
He, Rui,Wu, Shanchao,Tang, Haoming,Huo, Xiaohong,Sun, Zhenliang,Zhang, Wanbin
, p. 6183 - 6187 (2018/10/02)
An iridium-catalyzed asymmetric allylation of dioxindoles, 3-hydroxyoxindoles, regulated by prosthetic groups has been accomplished under mild conditions. The methodology is applicable to a diverse array of 3-hydroxyoxindole and cinnamyl acetate substrates. A range of 3-allyl-3-hydroxyoxindoles containing vicinal tetrasubstituted and trisubstituted stereocenters can be efficiently synthesized in one-step with excellent enantioselectivity (up to >99% enaniomeric excess (ee)) and good diastereoselectivity (up to 11:1 diastereomeric ratio (dr)).
Indium-mediated Palladium-catalyzed Allylic Alkylation of Isatins with Alkynes
Wu, Zijun,Fang, Xinxin,Leng, Yuning,Yao, Hequan,Lin, Aijun
, p. 1289 - 1295 (2018/02/21)
An unprecedented indium-mediated palladium-catalyzed allylic alkylation of isatins with alkynes is disclosed. This reaction provides a new, practical, and straightforward route to access 3-allyl-3-hydroxy-2-oxindoles in good yields with broad substrate scope and scalability, exhibiting high atom and step economy. A primary mechanistic study reveals that indium played two roles in the reaction, first as a reductant and second as a Lewis acid. Compared with previous methods, our strategy eliminated the steps for the separation and purification of the reaction intermediates, as well as pre-installing leaving groups to allylic substrates. Moreover, our reaction did not employ moisture-sensitive allylic metal species and stoichiometric oxidants. (Figure presented.).
The Power of Triplet and Singlet Oxygen in Synthesis: 2-Oxindoles, 3-Hydroxy-2-oxindoles, and Isatins from Furans
Triantafyllakis, Myron,Sfakianaki, Kalliopi,Kalaitzakis, Dimitris,Vassilikogiannakis, Georgios
supporting information, p. 3631 - 3634 (2018/06/26)
A straightforward synthesis of substituted 2-oxindoles, 3-hydroxy-2-oxindoles, and isatins has been developed. Easily accessible furans were transformed into tetrahydropyranopyrrolones by a singlet oxygen initiated cascade reaction sequence. An acid-catal
Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy
Buxton, Craig S.,Blakemore, David C.,Bower, John F.
, p. 13824 - 13828 (2017/10/24)
Nickel-catalyzed coupling of benzyl acrylates with activated ketones and imines provides γ-butyrolactones and lactams, respectively. The benzyl alcohol byproduct released during the lactonization/lactamization event is relayed to the next cycle where it serves as the reductant for C?C bond formation. This strategy represents a conceptually unique approach to transfer-hydrogenative C?C bond formation, thus providing examples of reductive heterocyclizations where hydrogen embedded within an alcohol leaving group facilitates turnover.
