72934-86-2

Upstream product

• 52562-19-3 2-isopropenylaniline 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 1885-29-6 anthranilic acid nitrile 
• 551-93-9 2-aminoacetophenone 
• 328956-41-8 (2-isopropenyl-phenyl)-carbamic acid methyl ester 
• 60249-97-0 1-(1-methylethenyl)-2-nitrobenzene 

Downstream Products

• 1198-37-4 2,4-dimethylquinoline 
• 402822-95-1 N-allyl-N-acetyl-2-isopropenylaniline 
• 1453542-20-5 N-but-3-enyl-N-(2-isopropenylphenyl)acetamide 
• 1453542-40-9 4-(2-isopropenylphenyl)-5-methyl-4-azabicyclo[3.1.0]hexane hydrochloride 
• 1453542-41-0 1-(2-isopropenylphenyl)-2,3-dimethylpyrrole 
• 1453542-35-2 5-(2-isopropenylanilino)-3-methyl-pentan-2-one 
• 607-66-9 4-methyl-1,2-dihydroquinolin-2-one 
• 1321594-66-4 2,4,4-trimethyl-4H-3,1-benzothiazine 
• 1321595-05-4 2-isopropenylthioacetanilide 
• 1236041-11-4 2,4-dimethyl-4-phenylselenomethyl-3,1-benzoxazine 

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.

Palladium(ii)-catalyzed vinylic geminal double C-H activation and alkyne annulation reaction: Synthesis of pentafulvenes

The first transition-metal-catalyzed vinylic geminal double C(sp2)-H activation and di-substituted alkyne annulation reaction is reported. This palladium(ii)-catalyzed, amide directed reaction of vinylic compounds with di-substituted alkynes offers an efficient synthetic path to pentafulvenes, which are very important compounds because of their bioactivity and interesting optical properties. A FeCl3-mediated transformation of pentafulvenes to fluorescent cyclopenta[b]quinolines is also developed.

Acid-Mediated Oxychalcogenation of o-Vinylanilides with N-(Arylthio/arylseleno)succinimides

An efficient acid-mediated oxythiolation of o-vinylanilides has been accomplished, employing N-(arylthio)succinimide as an electrophilic arylthiolating reagent for the synthesis of various arylthio tethered benzoxazine derivatives in good to excellent yie

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.

Synthesis of polycyclic aminocyclobutane systems by the rearrangement of N-(ortho-Vinylphenyl) 2-Azabicyclo[3.1.0]hexane derivatives

The acid-catalysed thermal rearrangements of a family of N-aryl 2-azabicyclo[3.1.0]hexanes is described. These substrates, designed in such a way that the aromatic system is conjugated with an alkene group located at the ortho position relative to the nitrogen atom, have been prepared by using an intramolecular Kulinkovich-de Meijere reaction. The rearrangements can then be conducted either under standard thermal conditions or with microwave activation. Depending on the conditions applied and the substitution pattern, dihydroquinoline or polycyclic aminocyclobutane derivatives can be obtained. A mechanistic discussion is provided, with the proposition of the initial protonation of the aminocyclopropane moiety to give an iminium intermediate. By analogy with related intermolecular reactions, the involvement of electrocyclic reactions among the series of elementary steps that follow is put forward. Small rings: The acid-catalysed rearrangement of bicyclic N-aryl aminocyclopropanes with an alkene group located at the ortho position, either under standard thermal conditions or with microwave activation, is described (see scheme). The method provides access to dihydroquinoline and polycyclic aminocyclobutane derivatives. By analogy with related intermolecular reactions, the involvement of an electrocyclic reaction is proposed. Copyright

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.

Sequential N-acylamide methylenation-enamide ring-closing metathesis: Construction of benzo-fused nitrogen heterocycles

The dimethyltitanocene methylenation of N-acylamides derived from ortho-vinylanilines, ortho-allylaniline, and ortho-vinylbenzylamine provides the corresponding enamides, which upon exposure to the second generation Grubbs ruthenium catalyst give access to indoles, 1,4-dihydroquinolines, and 1,2-dihydroisoquinolines, respectively. This sequential protocol also allows the synthesis of dihydrobenzoazepines, although the ring-closing metathesis (RCM) step is complicated by the alkene isomerization processes. From certain substrates, the direct annulation is observed in the titanium-mediated step, which is likely to occur through an olefin metathesis-intramolecular olefination sequence.

Synthesis of benzazetine derivatives by intramolecular iodoamination of o-(acylamino)styrene derivatives

The iodoamination of o-(acylamino)styrene derivatives using iodine and sodium hydrogencarbonate, producing 7-acyl-8-iodomethylbicyclo[4.2.0]-7-azaoct- 1,3,5-triene [1-acyl-2-(iodomethyl)benzazetine] derivatives, is described. Replacement of the iodo moiety by hydrogen or phenylthio group is also reported.

A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): Its application to the synthesis of key intermediates for anti-malarial agents

A method for synthesizing substituted quinolines using ruthenium-catalyzed ring-closing metathesis as a key step has been developed. Substituted 1,2-dihydroquinolines, 4-silyloxy-1,2-dihydroquinoline and 4-methoxy-1,2- dihydroquinoline, were successfully synthesized in excellent yields via ene-ene metathesis and silyl or alkyl enol ether-ene metathesis, respectively. The synthetic intermediates of the antimalarial agents quinine, chloroquine, and PPMP-quinine hybrid were efficiently synthesized by this methodology.