Divergent [5 + 1] Annulation of o-Aminobenzamides with Vinylene Carbonate as a Multifunctional Reagent

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 3, 2025

A divergent [5 + 1] cyclization reaction of o-aminobenzamides with vinylene carbonate has been developed, rapidly generating three types cyclic molecules including quinazolinones, 2-methylquinazolinones, and 2,3-dihydroquinazolinones high chemoselectivity. In this discovery, blooms as a multifunctional reagent to participate in cyclization. The potential new finding is further emphasized by assembling the benzothiazole heteroarene via [4 version tolerating bioactive units well.

Язык: Английский

Fe-Catalyzed Radical Trifluoromethylation and Cyclization of Ortho-Vinyl Enaminones with 1-(Trifluoromethyl)-1,3-benzo-[d][1,2]iodaoxol-3(1H)-one to Construct Functionalized Quinolines

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 19, 2025

Herein, we present a protocol for the construction of functionalized quinolines, i.e., 3-acyl-4-(2,2,2-trifluoro-ethyl)quinolines (ATFQLs) 4, from ortho-vinyl enaminones and 1-(trifluoromethyl)-1,3-benzo-[d][1,2]-iodaoxol-3(1H)-one, which was catalyzed by FeCp2 promoted FeCl3 (Lewis acid) additives in solvents (i.e., acetonitrile toluene). This strategy first utilized FeCp2-catalyzed functionalization alkenes with trifluoromethyl radicals. The intermediate formed captured ortho-iodobenzoate substrate, yielding 3, then underwent FeCl3-catalyzed elimination at higher temperature to form an α,β-unsaturated intermediate. subsequent intramolecular Michael reaction yielded final target compound 4. In summary, series ATFQLs 4 were synthesized through formation two bonds (C═C C-C).

Язык: Английский

Photocatalytic Three-Component Assemblies of Enaminones, α-Diazo Esters, and Nitriles for the Synthesis of N,N-Diacylated Glycine Esters

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 21, 2025

A facile method with simple starting materials, including enaminones, α-diazo esters, and nitriles, has been developed for the direct synthesis of N,N-diacyl glycine esters via visible light photocatalysis. The reaction involves a novel carbon-carbon bond cleavage in leading to products high tolerance variability substructures among all three components.

Язык: Английский