28558-62-5

Upstream product

• 91-56-5 indole-2,3-dione 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 3265-29-0 3-diazo-indolin-2-one 
• 22942-87-6 3-bromo-1,3-dihydro-2H-indol-2-one 
• 3265-14-3 3-diazo-1-methyl-1,3-dihydro-indol-2-one 
• 1379768-34-9 C₃₆H₃₁N₃O₁₀ 
• 1379768-33-8 C₃₆H₃₁N₃O₁₀ 
• 1379768-09-8 C₃₃H₃₃N₃O₉ 
• 1379768-07-6 C₃₃H₃₃N₃O₉ 
• 1379768-05-4 C₃₃H₃₃N₃O₁₀ 
• 1379768-03-2 C₃₃H₃₃N₃O₁₀ 
• 1379768-02-1 C₃₃H₃₁N₃O₁₀ 
• 1379768-01-0 C₃₃H₃₁N₃O₁₀ 
• 1379767-95-9 C₃₁H₂₉N₃O₉ 
• 1379767-93-7 C₃₁H₂₉N₃O₉ 
• 1379767-92-6 C₃₁H₂₉N₃O₁₀ 

Relevant academic research and scientific papers

Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2Hindol-2-ones using an Eschenmoser coupling reaction

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

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

Diastereoselective Palladium Catalyzed Carbenylative Amination of ortho-Vinylanilines with 3-Diazoindolin-2-ones

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.).

Dirhodium Coordination Polymers for Asymmetric Cyclopropanation of Diazooxindoles with Olefins: Synthesis and Spectroscopic Analysis

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

Photochemical O?H Functionalization Reactions of Cyclic Diazoamides

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.).

Efficient Synthesis of Spirooxindole Pyrrolones by a Rhodium(III)-Catalyzed C?H Activation/Carbene Insertion/Lossen Rearrangement Sequence

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.

Synthesis and evaluation of oxindoles as promising inhibitors of the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1

Indoleamine 2,3-dioxygenase 1 (IDO1) is considered as an important therapeutic target for the treatment of cancer, chronic infections and other diseases that are associated with immune suppression. Recent developments in understanding the catalytic mechanism of the IDO1 enzyme revealed that conversion of l-tryptophan (l-Trp) to N-formylkynurenine proceeded through an epoxide intermediate state. Accordingly, we synthesized a series of 3-substituted oxindoles from l-Trp, tryptamine and isatin. Compounds with C3-substituted oxindole moieties showed moderate inhibitory activity against the purified human IDO1 enzyme. Their optimization led to the identification of potent compounds, 6, 22, 23 and 25 (IC50 = 0.19 to 0.62 μM), which are competitive inhibitors of IDO1 with respect to l-Trp. These potent compounds also showed IDO1 inhibition potencies in the low-micromolar range (IC50 = 0.33-0.49 μM) in MDA-MB-231 cells. The cytotoxicity of these potent compounds was trivial in different model cancer (MDA-MB-231, A549 and HeLa) cells and macrophage (J774A.1) cells. Stronger selectivity for the IDO1 enzyme (124 to 210-fold) over the tryptophan 2,3-dioxygenase (TDO) enzyme was also observed for these compounds. These results suggest that the oxindole moiety of the compounds could mimic the epoxide intermediate state of l-Trp. Therefore, the structural simplicity and low-micromolar inhibition potencies of these 3-substituted oxindoles make them quite attractive for further investigation of IDO1 function and immunotherapeutic applications.

Synthesis of 3,3-dichloro-2-oxindoles from isatin-3-p-tosylhydrazones and (dichloroiodo)benzene

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.

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]

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.

Rhodium(II) acetate-catalyzed stereoselective synthesis, SAR and anti-HIV activity of novel oxindoles bearing cyclopropane ring

Novel oxindole derivatives bearing substituted cyclopropane ring have been designed on the basis of docking studies with HIV-1 RT using the software DS 2.5 and synthesized as probable NNRTIs against HIV-1 using rhodium(II) acetate-catalyzed stereoselectiv