3265-14-3

Basic information

• Product Name: 2H-Indol-2-one, 3-diazo-1,3-dihydro-1-methyl-
• CAS NO: 3265-14-3
• Molecular Formula: C9H7N3O
• Molecular Weight: 173.174
• Mol File: 3265-14-3.mol

Chemical Properties

• CAS DataBase Reference: 2H-Indol-2-one, 3-diazo-1,3-dihydro-1-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Indol-2-one, 3-diazo-1,3-dihydro-1-methyl-(3265-14-3)
• EPA Substance Registry System: 2H-Indol-2-one, 3-diazo-1,3-dihydro-1-methyl-(3265-14-3)

Safety Data

• Hazardous Substances Data: 3265-14-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
2H-Indol-2-one, 3-diazo-1,3-dihydro-1-methylis used as a diazo transfer reagent for the introduction of diazo groups into organic molecules, which is crucial in various chemical synthesis processes. Its reactivity makes it a valuable tool in the creation of new organic compounds and the modification of existing ones.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2H-Indol-2-one, 3-diazo-1,3-dihydro-1-methylis utilized to enhance the synthesis of complex organic molecules. Its ability to transfer diazo groups allows for the creation of a wide range of chemical products with diverse applications.
Used in Drug Discovery:
2H-Indol-2-one, 3-diazo-1,3-dihydro-1-methylmay also be employed in drug discovery, where its unique properties could contribute to the development of novel pharmaceutical agents. Its potential to form new organic reactions could lead to the discovery of new drug candidates with improved therapeutic properties.
Used in Research and Development:
In research and development settings, 2H-Indol-2-one, 3-diazo-1,3-dihydro-1-methylis used to explore and innovate new organic reactions. Its reactivity and structural features make it a subject of interest for scientists looking to expand the boundaries of organic chemistry and its applications.

Upstream product

• 3265-29-0 3-diazo-indolin-2-one 
• 74-88-4 methyl iodide 
• 61-70-1 N-methyl-2-indolinone 
• 339366-80-2 1-methyl-3-methylimino-1,3-dihydro-indol-2-one 
• 28558-62-5 4-methyl-N'-(2-oxoindolin-3-ylidene)benzenesulfonohydrazide 
• 74-83-9 methyl bromide 
• 3265-23-4 1-methyl-3-hydrazinoisatin 
• 91-56-5 indole-2,3-dione 
• 3265-25-6 N-methyl-3-tosylhydrazono-2-oxindole 
• 2058-74-4 1-methyl-1H-indole-2,3-dione 

Downstream Products

• 1356031-39-4 1,4-bis[(1'-methyl-1',3'-dihydro-1H-[3,3']biindolyl-2'-on)-1-yl]butane 
• 1356031-34-9 1,3-bis[(1'-methyl-1',3'-dihydro-1H-[3,3']biindolyl-2'-on)-1-yl]propane 
• 1356031-49-6 1,3-bis[((1'-methyl-1',3'-dihydro-1H-[3,3']biindolyl-2'-on)-1-yl)methyl]benzene 
• 1356031-44-1 1,2-bis[((1'-methyl-1',3'-dihydro-1H-[3,3']biindolyl-2'-on)-1-yl)methyl]benzene 
• 1379767-82-4 C₂₇H₃₂N₂O₇ 
• 1379767-81-3 C₂₇H₃₂N₂O₇ 
• 1379767-83-5 C₂₇H₃₂N₂O₆ 
• 1379767-70-0 C₂₅H₂₈N₂O₇ 
• 1379767-67-5 C₂₅H₂₈N₂O₇ 
• 1379767-72-2 C₂₅H₂₈N₂O₆ 
• 1379767-71-1 C₂₅H₂₈N₂O₆ 
• 1379767-79-9 C₂₇H₃₀N₂O₇ 

Relevant articles and documents

Rh2(OAc)4-catalyzed regioselective intermolecular C-H insertion reactions: Novel synthesis of 2-pyrrol-3′-yloxindoles

Regioselective synthesis of 2-pyrrol-3′-yloxindoles has been achieved by the reactions of cyclic diazo carbonyl compounds la-e with pyrrole and substituted pyrroles (2a-d) in the presence of rhodium(II) acetate catalyst via intermolecular C-H insertion reaction.

Stereoselective epoxide generation with cyclic rhodium carbenoids: A new access to spiro-indolooxiranes

The reaction of cyclic diazoamides with aryl aldehydes catalyzed by rhodium(II) acetate leads to intermolecular stereoselective epoxide ring formation. A series of spiro-indolooxiranes has been synthesized following the described method in a facile manner. The use of aryl dialdehydes in the course of reaction of cyclic diazoamide resulted the formation of bis-spiro- indolooxiranes.

Visible-Light-Mediated Cyclopropanation Reactions of 3-Diazooxindoles with Arenes

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.

Highly diastereoselective synthesis of dispiro[1,4-dithiane/dithiepane] bisoxindoles via Stevens rearrangement

Synthesis of dispiro[1,4-dithianes/dithiepanes]bisoxindoles from the reaction of 3-diazo-2-oxindoles and spiro-1,3-dithiolaneoxindole or -1,3-dithianeoxindole derivatives in the presence of rhodium(II) acetate dimer as a catalyst was demonstrated under mild conditions in a highly diastereoselective manner. These dispiro-compounds were obtained via intermolecular sulfonium ylides and followed by Stevens rearrangement.

Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation

We develop a visible light-promoted divergent cycloaddition of α-diazo esters with hexahydro-1,3,5-triazines, leading to a series of aziridine and imidazolidine frameworks in average good yield, by simply changing the reaction media used. It is noteworthy that the reaction occurs under sole visible light irradiation without the need for exogenous photoredox catalysts. More significantly, a reasonable reaction mechanism was proposed on the basis of the control experiments and density functional theory calculation results.

Copper-Catalyzed Oxidation of Hydrazones to Diazo Compounds Using Oxygen as the Terminal Oxidant

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.

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

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.

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.).

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.).