106012-41-3

Upstream product

• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 110674-68-5 1-phenyl-N-(2-(prop-1-en-2-yl)phenyl)methanimine 
• 1885-29-6 anthranilic acid nitrile 
• 6011-26-3 2'-acetylbenzanilide 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 60249-97-0 1-(1-methylethenyl)-2-nitrobenzene 
• 106012-47-9 4-Methyl-4-methylsulfanylmethyl-2-phenyl-4H-benzo[d][1,3]oxazine 
• 52562-19-3 2-isopropenylaniline 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 551-93-9 2-aminoacetophenone 

Downstream Products

• 858621-37-1 7-benzoyl-8-iodomethyl-8-methylbicyclo[4.2.0]-7-azaocta-1,3,5-triene 
• 1392323-24-8 C₁₆H₁₄BrNO 
• 106012-48-0 4,4-dimethyl-2-phenyl-4H-benzo[d][1,3]oxazine 
• 106012-47-9 4-Methyl-4-methylsulfanylmethyl-2-phenyl-4H-benzo[d][1,3]oxazine 
• 119449-57-9 N-(2-Isopropenyl-phenyl)-benzimidic acid ethyl ester 

Relevant academic research and scientific papers

Novel formation of indoles and 3,1-benzoxazines from o-alkenylanilides and dimethyl(methylthio)sulfonium trifluoromethanesulfonate

The reaction of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) with o-allylphenol gave 2-methylthiomethyl-2,3-dihydrobenzofuran in 97% yield. The reaction of DMTST with N-tosyl-o-isopropenylanilide followed by the addition of aq sodium carbonate afforded N-tosyl-3-methylindole in 88% yield, whereas N-tosyl-o-vinylanilide afforded N-tosylindoline in 85% yield.

Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines

Visible-light-excited 9,10-phenanthrenequinone (PQ*) was used as a photocatalyst for the synthesis of polysubstituted quinolines via the electrocyclization of 2-vinylarylimines. Up to quantitative yields of 2,4-disubstituted quinolines were received after 1 h of excitation with blue LEDs at room temperature when MgCO3 was used as an additive in DCM. On the basis of experimental and DFT studies, we propose that PQ? induces one-electron oxidation of the imine substrate that triggers the electrocyclization mechanism.

Trifluoromethylthio-containing tryptamine derivative and preparation thereof, and application in prevention and treatment of plant viruses and pathogenic bacteria

The invention relates to a trifluoromethylthio-containing tryptamine derivative I and a preparation method thereof, and application of the trifluoromethylthio-containing tryptamine derivative I in prevention and treatment of plant viruses and pathogenic bacteria. According to the invention, the trifluoromethylthio-containing tryptamine derivative I shows anti-plant virus activity, wherein the inhibition rate of the derivative containing chlorine atoms in the structure on tobacco mosaic virus (TMV) can reach the level equivalent to that of virazole; and the compound also shows certain anti-plant pathogenic bacterium activity, and has relatively good inhibitory activity on physalospora piricola.

Electrochemical oxidative radical cascade cyclization of olefinic amides and thiophenols towards the synthesis of sulfurated benzoxazines, oxazolines and iminoisobenzofurans

Heterocycles containing N and O are important structures in pharmaceuticals, agrochemicals and functional molecules. The synthesis of these compounds usually requires complex substrates and harsh reaction conditions. Herein, we introduce a mild and efficient electrochemical oxidative strategy to construct benzoxazines, oxazolines and iminoisobenzofurans without the requirement of a transition-metal catalyst and an external oxidant. In a simple undivided cell, various olefinic amides and thiophenols/diselenides react to generate 69 examples of thiolation and selenylation heterocycles in up to 83% yields. Furthermore, this radical cascade reaction provided a facile method for constructing C-S/C-Se and C-O bonds in one step.

Efficient synthesis of SCF3-substituted tryptanthrins by a radical tandem cyclization

Herein, we report a new, efficient and atom-economical strategy for the synthesis of SCF3-substituted tryptanthrin derivatives. These previously unreported derivatives were obtained by means of a radical tandem cyclization. The reaction was triggered by addition of a SCF3 radical to a carbon-carbon double bond and involved the formation of a C(sp3)-SCF3 bond, a C(sp2)-C bond, and a C(sp2)-N bond. This method has mild conditions and a wide range of substrates which is particularly useful for the preparation of substituted indolquinazoline derivatives that widely exist in many natural products, but are not easy to obtain by conventional approaches.

The synthesis of sulfonated 4: H -3,1-benzoxazines via an electro-chemical radical cascade cyclization

A new route for the synthesis of sulfonated 4H-3,1-benzoxazines has been accomplished by electrochemical radical cascade cyclizations of styrenyl amides with sulfonylhydrazines. This process demonstrates a wide substrate scope with diverse functional group compatibility under metal- and external oxidant-free conditions at ambient temperature.

Experimental and Computational Studies on Cp*CyRh(III)/KOPiv-Catalyzed Intramolecular Dehydrogenative Cross-Couplings for Building Eight-Membered Sultam/Lactam Frameworks

Described herein is an unusual Cp*CyRh(III)-catalyzed intramolecular site-specific aryl C-H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams with broad substrate/functional group tolerance. Experimental and computational studies reveal that such a transformation involves a unique PivOH-assisted aryl C-H activation/alkene insertion/β-H elimination/hydrogen-transfer process involving the Rh(III)-hydride species as the active intermediate with the concomitant release of H2 as the major byproduct, thus enabling the developed Cp*CyRh(III) catalysis with redox-neutral and highly atom-economical features.

Water-Soluble Hypervalent Iodine(III) Having an I-N Bond. A Reagent for the Synthesis of Indoles

A readily accessible and bench-stable water-soluble hypervalent iodine(III) reagent (phenyliodonio)sulfamate (PISA) with an I-N bond was synthesized, and its structure was characterized by X-ray crystallography. With PISA, various indoles were synthesized via C-H amination of 2-alkenylanilines involving an aryl migration/intramolecular cyclization cascade with excellent regioselectivity in aqueous CH3CN. Notably, using this new method as the key step, not only two drug molecules, indometacin and zidometacin, but also another bioactive molecule, pravadoline, were synthesized.

Organocatalytic Synthesis of Oxazolines and Dihydrooxazines from Allyl-Amides: Bypassing the Inherent Regioselectivity of the Cyclization

A selective and efficient methodology for the construction of either oxazolines or dihydrooxazines from the corresponding allyl-amides is reported. Bypassing the inherent selectivity of the cyclization and depending on the substitution pattern of the substrate, a selective epoxidation-cyclization was developed leading to either the five-membered or the six-membered ring, upon simple and complementary reaction conditions. The cyclization products were obtained in good to excellent yields and high selectivities. (Figure presented.).

Copper-catalyzed trifluoromethylation of alkenes: Synthesis of trifluoromethylated benzoxazines

A simple base and ligand free copper catalyzed method for the construction of trifluoromethylated benzoxazines has been developed by using Umemoto's reagent. It involves the oxidative difunctionalization of alkenes through tandem C-O and C-CF3 bond formations. Furthermore, synthesized benzoxazines were selectively converted into trifluoromethylated allylic and (E)-vinylic benzamides by the treatment of KOtBu and CH3Li, respectively.