3265-29-0Relevant articles and documents
Photochemically Induced Ring Opening of Spirocyclopropyl Oxindoles: Evidence for a Triplet 1,3-Diradical Intermediate and Deracemization by a Chiral Sensitizer
Bach, Thorsten,Bauer, Andreas,Jandl, Christian,Kutta, Roger J.,Li, Xinyao,Nuernberger, Patrick
, p. 21640 - 21647 (2020)
The photochemical deracemization of spiro[cyclopropane-1,3′-indolin]-2′-ones (spirocyclopropyl oxindoles) was studied. The corresponding 2,2-dichloro compound is configurationally labile upon direct irradiation at λ=350 nm and upon irradiation at λ=405 nm
Copper-Catalyzed Oxidation of Hydrazones to Diazo Compounds Using Oxygen as the Terminal Oxidant
Liu, Wenbin,Twilton, Jack,Wei, Bo,Lee, Maizie,Hopkins, Melissa N.,Bacsa, John,Stahl, Shannon S.,Davies, Huw M. L.
, p. 2676 - 2683 (2021/03/03)
A mild method for accessing diazo compounds via aerobic oxidation of hydrazones is described. This catalytic transformation employs a Cu(OAc)2/pyridine catalyst and molecular oxygen from ambient air as the terminal oxidant, generating water as the sole byproduct and affording the desired diazo compounds within minutes at room temperature. A broad array of electronically diverse aryldiazo esters, ketones, and amides can be accessed. Pyridine dramatically enhances the rate of the reaction by solubilizing the copper catalyst and serving as the Br?nsted base in the turnover-limiting proton-coupled oxidation of hydrazone by copper(II). Insights gained from mechanistic studies led to expansion of the scope of this method to include diaryl hydrazones, delivering diaryl diazomethane derivatives, which cannot be accessed via established diazo transfer methods. The products of this method may be employed in rhodium carbene catalysis without isolation of the diazo intermediate to afford cyclopropane products in good yield with high enantioselectivity.
Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2Hindol-2-ones using an Eschenmoser coupling reaction
Marek, Luká?,Kolman, Luká?,Váňa, Ji?í,Svoboda, Jan,Hanusek, Ji?í
supporting information, p. 527 - 539 (2021/03/31)
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.
Construction of 2-alkynyl aza-spiro[4,5]indole scaffolds: Via sequential C-H activations for modular click chemistry libraries
Zhang, Jun,Wang, Mengmeng,Wang, Huiying,Xu, Hui,Chen, Junjie,Guo, Ziqiong,Ma, Biao,Ban, Shu-Rong,Dai, Hui-Xiong
supporting information, p. 8656 - 8659 (2021/09/04)
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
Synthesis of Isatin-Hydrazones from 3-Diazo Oxindoles and Sulfoxonium Ylides under Catalyst- and Additive-Free Conditions
Tian, Yu,Zhang, Zunting,Wang, Tao
supporting information, p. 1592 - 1595 (2021/02/26)
A facile synthesis of isatin-hydrazones from 3-diazo oxindoles and sulfoxonium ylides under catalyst- and additive-free conditions is described. A plausible reaction pathway is proposed for the transformation, in which diazo compounds play as electrophile
Visible-Light-Mediated Cyclopropanation Reactions of 3-Diazooxindoles with Arenes
Zhao, Shuai,Chen, Xiang-Xiang,Gao, Nan,Qian, Mingcheng,Chen, Xin
, p. 7131 - 7140 (2021/05/06)
The cyclopropanation reaction of 3-diazooxindoles with arenes was first accomplished using visible-light irradiation. A series of spiro[norcaradiene-7,3′-indolin]-2′-ones were synthesized for the first time in high yields and with excellent diastereoselectivities. The synthetic usefulness of this catalyst-free photochemical methodology is illustrated by the further controllable rearrangement and epoxidation reactions.
Indolocyclobutane skeleton compound, and synthesis method and application thereof
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Paragraph 0126-0129; 0135, (2021/07/08)
The invention discloses an indolocyclobutane skeleton compound as well as a synthesis method and application thereof. The indolocyclobutane skeleton compound comprises a compound with a structure as shown in a formula I or a formula II which is described
Dirhodium Coordination Polymers for Asymmetric Cyclopropanation of Diazooxindoles with Olefins: Synthesis and Spectroscopic Analysis
Breitzke, Hergen,Brodrecht, Martin,Buntkowsky, Gerd,Gutmann, Torsten,Herr, Kevin,Hofmann, Kathrin,Li, Zhenzhong,Limbach, Hans-Heinrich,R?sler, Lorenz
, p. 1737 - 1746 (2020/09/02)
A facile approach is reported for the preparation of dirhodium coordination polymers [Rh2(L1)2]n (Rh2-L1) and [Rh2(L2)2]n (Rh2-L2; L1=N,N’-(pyromellitoyl)-bis-L-phenyl
Diastereoselective Palladium Catalyzed Carbenylative Amination of ortho-Vinylanilines with 3-Diazoindolin-2-ones
Reddy, Angula Chandra Shekar,Reddy, Palagulla Maheswar,Anbarasan, Pazhamalai
supporting information, p. 801 - 806 (2020/01/25)
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.).
Photochemical O?H Functionalization Reactions of Cyclic Diazoamides
Empel, Claire,Jana, Sripati,Koenigs, Rene M.,Verspeek, Dennis
supporting information, p. 4716 - 4722 (2020/09/23)
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.).
