Visible-light-induced organophotocatalytic and singlet oxygen-initiated domino construction of 1,4-dihydropyridines, C-3 functionalized spiro[indoline-3,4'-pyridines] and C-11 functionalized spiro[indeno-[1,2-b]quinoxaline-11,4'-pyridines].

A highly efficient pot, atom, and step economical method for the construction of pharmacologically potent structurally functionalized 1,4-dihydropyridines, quaternary centered C-3 functionalized spiro[indoline-3,4'-pyridines], and C-11 functionalized spiro[indeno[1,2-b]quinoxaline-11,4'-pyridines] via rose bengal photoredox catalysis under blue LED irradiation in an aqueous medium at room temperature has been developed. The products were isolated in excellent yields within a short reaction time for a variety of functional groups under transition metal- and ligand-free energy-efficient conditions in a green solvent system with high reaction mass efficiency and process mass intensity, which are the key advantages of the current work.

Brønsted acid catalyzed mechanochemical domino multicomponent reactions by employing liquid assisted grindstone chemistry.

Here, we have demonstrated a metal-free energy-efficient mechanochemical approach for expedient access to a diverse set of 2-amino-3-cyano-aryl/heteroaryl-4H-chromenes, tetrahydrospiro[chromene-3,4'-indoline], 2,2'-aryl/heteroarylmethylene-bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) as well as tetrahydro-1H-xanthen-1-one by employing the reactivity of 5,5-dimethylcyclohexane-1,3-dione/cyclohexane-1,3-dione with TsOH⋅H2O as Brønsted acid catalyst under water-assisted grinding conditions at ambient temperature. The ability to accomplish multiple C-C, C=C, C-O, and C-N bonds from readily available starting materials via a domino multicomponent strategy in the absence of metal-catalyst as well as volatile organic solvents with an immediate reduction in the cost of the transformation without necessitates complex operational procedures, features the significant highlights of this approach. The excellent yield of the products, broad functional group tolerances, easy set-up, column-free, scalable synthesis with ultralow catalyst loading, short reaction time, waste-free, ligand-free, and toxic-free, are other notable advantages of this approach. The greenness and sustainability of the protocol were also established by demonstrating several green metrics parameters.

Stereoselective synthesis of CF3-containing spirocyclic-oxindoles using N-2,2,2-trifluoroethylisatin ketimines: an update.

The introduction of fluorine-containing groups into organic molecules either changes or improves the characteristics of the target compounds. On the other hand, spirocyclic-oxindoles featuring C-3 functionalized sp3-hybridized carbon atoms of three-dimensional orthogonally shaped molecules were well recognized in the core structure of varied natural products and synthetic pharmaceutical targets. Consequently, the construction of spirooxindoles by an elegant synthetic approach with efficient stereocontrol has received tremendous interest over the past decades. In this context of the synergic combination of the features associated with fluorine-containing compounds and the synthetic and medicinal efficiency associated with spirooxindoles, the stereodivergent installation of CF3 groups embedded with spirooxindoles is of increasing academic and scientific interest. This mini-review article is dedicated to demonstrating a critical overview of the recent stereoselective synthesis of spirocyclic-oxindoles featuring trifluoromethyl groups by employing the reactivity of N-2,2,2-trifluoroethylisatin ketimines as an efficient and easily prepared synthon, and covers the literature reports from 2020 to date. Besides exploring the advancements accomplished in this area, we also investigate the limitations associated with reaction discovery, mechanistic rationalization, and future applications.

Recent advances and prospects in the organocatalytic synthesis of quinazolinones.

Quinazolinone, a bicyclic compound, comprises a pyrimidine ring fused at 4´ and 8´ positions with a benzene ring and constitutes a substantial class of nitrogen-containing heterocyclic compounds on account of their frequent existence in the key fragments of many natural alkaloids and pharmaceutically active components. Consequently, tremendous efforts have been subjected to the elegant construction of these compounds and have recently received immense interest in synthetic and medicinal chemistry. The domain of synthetic organic chemistry has grown significantly over the past few decades for the construction of highly functionalized therapeutically potential complex molecular structures with the aid of small organic molecules by replacing transition-metal catalysis. The rapid access to this heterocycle by means of organocatalytic strategy has provided new alternatives from the viewpoint of synthetic and green chemistry. In this review article, we have demonstrated a clear presentation of the recent organocatalytic synthesis of quinazolinones of potential therapeutic interests and covered the literature from 2015 to date. In addition to these, a clear presentation and understanding of the mechanistic aspects, features, and limitations of the developed reaction methodologies have been highlighted.