119449-53-5

Upstream product

• 1885-29-6 anthranilic acid nitrile 
• 551-93-9 2-aminoacetophenone 
• 527-69-5 2-furancarbonyl chloride 
• 52562-19-3 2-isopropenylaniline 

Downstream Products

• 119449-64-8 2-(furan-2-yl)-4,4-dimethyl-4H-benzo[d][1,3]oxazine 
• 119449-58-0 N-(2-Isopropenyl-phenyl)-furan-2-carboximidic acid ethyl ester 

Relevant academic research and scientific papers

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.

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.

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.

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.

A CONVENIENT SYNTHESIS OF SUBSTITUTED QUINOLINES BY THERMAL OR PHOTOCHEMICAL ELECTROCYCLIC REARRANGEMENT OF o-VINYL IMIDATES UNDER NON-ACIDIC CONDITIONS.

Imidates 4a-e, Table 1, were prepared by treatment of amides 3a-e with Et3O(1+)BF4(1-) in the presence of excess Na2HPO4.These underwent smooth rearrangement to quinolines 5a-e by thermal or photochemical activation.