- Construction of 2-alkynyl aza-spiro[4,5]indole scaffolds: Via sequential C-H activations for modular click chemistry libraries
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Herein, we have developed a strategy of sequential C-H activations of indole to construct novel 2-alkynyl aza-spiro[4,5]indole scaffolds, which incorporated both alkyne and spiro-units into indole. Gram-scale synthesis and a one-pot, three-step synthesis demonstrated the utility of this protocol. Hybrid conjugates with an oseltamivir derivative further offered a powerful tool for the construction of a versatile spiroindole-containing library via click chemistry. This journal is
- Zhang, Jun,Wang, Mengmeng,Wang, Huiying,Xu, Hui,Chen, Junjie,Guo, Ziqiong,Ma, Biao,Ban, Shu-Rong,Dai, Hui-Xiong
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p. 8656 - 8659
(2021/09/04)
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- Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2Hindol-2-ones using an Eschenmoser coupling reaction
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A highly modular method for the synthesis of (Z)-3-[amino(phenyl/methyl)methylidene]-1,3-dihydro-2H-indol-2-ones starting from easily available 3-bromooxindoles or (2-oxoindolin-3-yl)triflate and thioacetamides or thiobenzamides is described. A series of 49 compounds, several of which have previously been shown to possess significant tyrosin kinase inhibiting activity, was prepared in yields varying mostly from 70 to 97% and always surpassing those obtained by other published methods. The method includes an Eschenmoser coupling reaction, which is very feasible (even without using a thiophile except tertiary amides) and scalable. The (Z)configuration of all products was confirmed by NMR techniques.
- Marek, Luká?,Kolman, Luká?,Váňa, Ji?í,Svoboda, Jan,Hanusek, Ji?í
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supporting information
p. 527 - 539
(2021/03/31)
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- Diastereoselective Palladium Catalyzed Carbenylative Amination of ortho-Vinylanilines with 3-Diazoindolin-2-ones
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A diastereoselective palladium catalyzed carbenylative amination of ortho-vinylaniline with 3-diazoindolines-2-one have been accomplished for the synthesis of various tetrasubstituted indoline fused spirooxindole with good yields and diastereoselectivity. Notable features of the method include construction of two contiguous tetrasubstituted carbon stereocenters via C?N and C?C bond formation in single operation, wide functional group tolerance and high atom and step economy. Importantly, the present reaction was also extended to one-pot conversion of tosylhydrazones and ortho-vinylanilines to spirooxindole derivatives. (Figure presented.).
- Reddy, Angula Chandra Shekar,Reddy, Palagulla Maheswar,Anbarasan, Pazhamalai
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p. 801 - 806
(2020/01/25)
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- Photochemical O?H Functionalization Reactions of Cyclic Diazoamides
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Herein, we describe the photochemical O?H functionalization reaction of acidic alcohols with cyclic diazoamides. We studied the O?H functionalization reaction of different fluorinated and non-fluorinated alcohols to give the corresponding ether products in high yields (43 examples, up to 97% yield). Furthermore, we performed studies to evaluate a photoexcited proton transfer reaction pathway in comparison to classic carbene transfer reactions. (Figure presented.).
- Empel, Claire,Jana, Sripati,Koenigs, Rene M.,Verspeek, Dennis
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supporting information
p. 4716 - 4722
(2020/09/23)
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- Efficient Synthesis of Spirooxindole Pyrrolones by a Rhodium(III)-Catalyzed C?H Activation/Carbene Insertion/Lossen Rearrangement Sequence
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A rhodium(III)-catalyzed domino annulation of simple olefins with diazo oxindoles to give spirooxindole pyrrolone products is described. This reaction can be formally viewed as the result of an anomalous tandem C?H activation, carbene insertion, Lossen rearrangement, and a nucleophilic addition process. The potential utility of this reaction was further demonstrated by the late-stage diversification of drug molecules.
- Ma, Biao,Wu, Peng,Wang, Xing,Wang, Zhengyu,Lin, Hai-Xia,Dai, Hui-Xiong
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p. 13335 - 13339
(2019/08/20)
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- Stereoselective construction of α-tetralone-fused spirooxindoles via Pd-catalyzed domino carbene migratory insertion/conjugate addition sequence
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An efficient diastereoselective synthesis of α- tetralone-fused spirooxindoles is reported. The Pd-catalyzed domino reaction proceeds through a carbene migratory insertion followed by a 6-endo-trig mode of conjugate addition sequence from easily accessibl
- Arunprasath, Dhanarajan,Bala, Balasubramanian Devi,Sekar, Govindasamy
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supporting information
p. 5280 - 5283
(2017/11/06)
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- Diastereoselective Construction of 3-Aminooxindoles with Adjacent Stereocenters: Stereocontrolled Addition of γ-Substituted Allylindiums to Isatin Ketimines
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The diastereoselective construction of 3-allyl-3-aminooxindoles that have two adjacent stereocenters has been achieved by the In-promoted Barbier-type addition of γ-substituted allylic halides to the C=N bond of isatin ketimines. The reactions of cinnamyl
- Aslam, Nayyar Ahmad,Babu, Srinivasarao Arulananda,Rani, Soniya,Mahajan, Shivam,Solanki, Jagmohan,Yasuda, Makoto,Baba, Akio
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p. 4168 - 4189
(2015/06/30)
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- Synthesis of 3,3-dichloro-2-oxindoles from isatin-3-p-tosylhydrazones and (dichloroiodo)benzene
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Abstract A series of aryl- and N-substituted isatin derivatives were converted to the corresponding isatin-3-p-tosylhydrazones, and these were subjected to a Lewis base-catalyzed chlorination reaction that employs the hypervalent chlorinating agent PhICl2. The discovery of p-tosylhydrazones as chlorination precursors has expanded the functional group tolerance of the chlorination reaction to now include carbamates, acetamides, and sulfonates. Additionally, this allowed us to circumvent the use of the diazo group in our chlorination reaction, and offers a new avenue for exploring our two-step deoxygenative dihalogenation reaction. We also disclose the use of PhICl2 for the oxidative chlorination of sulfinates to the corresponding sulfonyl chlorides.
- Hepples, Charlotte,Murphy, Graham K.
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supporting information
p. 4971 - 4974
(2015/08/04)
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- One-Pot Tandem Diastereoselective and Enantioselective Synthesis of Functionalized Oxindole-Fused Spiropyrazolidine Frameworks
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A highly efficient palladium(0)-catalyzed asymmetric [3+2] cycloaddition using 3-diazooxindoles serving as dipolarophiles affords functionalized pyrazolidine derivatives in an atom-economical way. In addition, by trapping the pyrazolidine derivatives with maleimides, the corresponding spiropyrazolidine oxindoles containing multiple stereogenic centers have been obtained in high yields along with moderate to good levels of diastereoselectivity and enantioselectivity under mild conditions. Thus, a novel three-component one-pot tandem reaction has been developed.
- Mei, Liang-Yong,Tang, Xiang-Ying,Shi, Min
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supporting information
p. 13136 - 13142
(2016/02/19)
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- Br?nsted acid/rhodium(II) cooperative catalytic asymmetric three-component aldol-type reaction for the synthesis of 3-amino oxindoles
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Cooperation is key! Chiral Br?nsted acid/rhodium(II) cooperative catalysis enabled an enantioselective three-component aldol-type reaction of 3-diazo oxindoles and anilines with glyoxylates to give highly functionalized and structurally diverse 3-amino oxindoles in high stereoselectivity (>20:1 d.r., 99 % ee; see scheme). Copyright
- Ren, Lei,Lian, Xiao-Lei,Gong, Liu-Zhu
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supporting information
p. 3315 - 3318
(2013/07/11)
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- Diastereoselective synthesis of β-Lactam-oxindole hybrids through a three-component reaction of azetidine-2,3-diones, α-diazo-oxindoles, and alcohols catalyzed by [Rh2(OAc)4]
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β-Lactam-oxindole hybrids have been synthesized in good yields in a one-pot procedure through efficient and stereoselective capture of an oxonium ylide with azetidine-2,3-diones. The reaction allows high to moderate control of stereoselectivity, depending on the 3-diazo-oxindole precursor and the hydroxylic compound used. Two new quaternary stereogenic centers were formed; the stereochemistry at the C-3 quaternary center was controlled by a bulky substituent at C-4, whereas the stereoselectivity in the adjacent second quaternary stereogenic center was controlled by the α-diazo-oxindole. The stereochemistry of both quaternary centers has been unambiguously assigned by single-crystal X-ray diffraction. Densely functionalized β-lactam-oxindole hybrids have been prepared in a one-pot, multicomponent reaction between azetidine-2,3-diones, α-diazo-oxindoles, and alcohols. Two new stereogenic centers were formed; the stereochemistry at the new C-3 quaternary center was controlled by a bulky substituent at C-4, whereas the second new stereogenic center was controlled by the α-diazo-oxindole.
- Alcaide, Benito,Almendros, Pedro,Aragoncillo, Cristina,Callejo, Ricardo,Ruiz, M. Pilar,Torres, M. Rosario
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p. 2359 - 2366
(2012/06/04)
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