Dicarbonyl compounds in the synthesis of heterocycles under green conditions

Carbon–carbon and carbon-heteroatom bond forming reactions are strategically employed for the generation of a variety of heterocyclic systems. This class of compounds represents the most general structural unit, present in many natural compounds. They are recognized for their valuable biologically properties and wide range of applications in medicinal, pharmaceutical, and other related fields of chemistry. This is an updated review on the use of dicarbonyl compounds under environmentally friendly conditions to access a series of heterocyclic structures, e.g., quinoxaline, quinazolinones, benzochalcogenazoles, indoles, among others. Synthetic protocols involving copper-catalyzed, multicomponent and cascade reactions, decarboxylative cyclization, recycling of CO2, and electrochemical approaches are presented and discussed.

N-Iodosuccinimide-Promoted Selective Construction of Cyclopropyl and Dihydrofuranyl Spirooxindoles from Alkylidene Oxindoles and Annular β-Dicarbonyl Compounds

An efficient N-iodosuccinimide-promoted cyclization of readily available alkylidene oxindoles with annular β-dicarbonyl compounds has been demonstrated. With five-membered cyclic β-dicarbonyl compounds as the starting materials, a series of cyclopropyl oxindoles can be obtained in good to excellent yields, whereas it almost quantitatively affords dihydrofuranyl spirooxindoles when six- or seven-membered cyclic β-dicarbonyl compounds are employed. This protocol provides a new alternative to the practical synthesis of structurally diverse spirooxindoles.

Correction: Electrochemically-mediated C–H functionalization of allenes and 1,3-dicarbonyl compounds to construct tetrasubstituted furans

Correction for ‘Electrochemically-mediated C–H functionalization of allenes and 1,3-dicarbonyl compounds to construct tetrasubstituted furans’ by Mu-Xue He et al., Org. Chem. Front., 2022, DOI: 10.1039/d1qo01458g.

Electrochemically-mediated C-H functionalization of allenes and 1,3-dicarbonyl compounds to construct tetrasubstituted furans

C-H functionalization of allenes is an available strategy to construct heterocyclic compounds. Herein we propose a sus-tainable electrocatalytic C-H activation for the synthesis of novel highly functionalized tetrasubstituted furans, which...

A Metal-Free Strategy for the Cross-Dehydrogenative Coupling of the 1, 3-Dicarbonyl Compounds with 2-Methoxyethanol

Here, we report a metal-free approach for the construction of methylene-bridged bis-1,3-dicarbonyl compounds via cross-dehydrogenative coupling of 1,3-dicarbonyl compounds with 2-methoxyethanol. In addition, we have extended this methodology to synthesize...

Ultrasound-assisted synthesis of β-enaminone derivatives via Tin(Ⅳ)-catalyzed addition reaction from β-dicarbonyl compounds with nitriles

An efficient and eco-friendly approach for the synthesis of β-enaminone derivatives is described, which is through the addition of nitriles with β-dicarbonyl compounds under ultrasound irradiation condition at room temperature. The scope and limitation of this strategy are also discussed. A variety of substituted amides can be obtained in moderate to good yields. We hope that this protocol for the efficient synthesis of β-enaminones will offer insights in further investigations.