A versatile approach for one-pot synthesis of hybridized quinolines linked to fused N-containing heterocycles in water.

Here, highly efficient one-pot protocols for the synthesis of structurally diverse fused N-containing heterocycles containing 2-chloroquinoline employing 1,1-bis(methylsulfanyl)-2-nitroethene, diamines, 2-chloroquinoline-3-carbaldehydes and dimedone/Meldrum's acid in green media in the absence of catalyst are reported. The current report proposes sustainable, simple, four-component and straightforward strategies for generating interesting N-containing heterocyclic compounds from a range of diamines and 2-chloroquinoline-3-carbaldehydes. The utilization of water as green media furnishes sustainability by preventing the usage of toxic solvent. A range of quinoline-containing aldehydes and diamines can be converted to two types of products with respect to using dimedone or Meldrum's acid via an inexpensive, one-pot and easy route.

Pyrazole-promoted synthesis of pyrrolo[3,4-c] quinoline-1,3-diones in a novel diketene-based reaction.

We describe the first classic example of green synthesis of pyrrolo[3,4-c]quinolones scaffolds by catalyst-free unusual reaction of diketene, isatin, and primary amines in ethanol in the presence of pyrazole as a promoter for 4 h. The whole structure of the new product was confirmed by X-ray analysis. The overall transformation involves the cleavage and generation of multiple carbon-nitrogen and carbon-carbon bonds. This report represents a simple and straightforward approach for the synthesis of pyrrolo[3,4-c]quinoline-1,3-diones, which has significant advantages like readily available precursors, non-use of toxic solvent, operational simplicity, mild conditions, good atom economy, and excellent yields; therefore it provides a green and sustainable strategy for access to a range of interesting N-containing heterocyclic compounds in medicinal and organic chemistry.

Cascade process for direct synthesis of indeno[1,2-b]furans and indeno[1,2-b]pyrroles from diketene and ninhydrin.

Novel and efficient multicomponent reactions (MCRs) involving diketene, ninhydrin (indane-1,2,3-trione) and one primary amine (3CR) or two different primary amines (4CR) were achieved for the successful synthesis of dihydro-4H-indeno[1,2-b]furan-3-carboxamides or tetrahydroindeno[1,2-b]pyrrole-3-carboxamides, respectively. The merits of this method are highlighted by using either commercially available or easily accessible starting materials, operational simplicity, facile workup procedure, efficient usage of all the reactants, tolerance of a variety of functional groups and ability to conduct under un-catalyzed reaction condition. The products were also isolated by just decantation of the solvent, and for the purification column chromatography was non-required.

A novel pseudo six-component synthesis of functionalized pyrazoles in ethanol by cascade reaction.

Novel-substituted pyrazoles were synthesized using an aminal-based approach. The key steps in the synthetic strategy involve the formation of 1,1-dihydrazino-2-nitroethylene from hydrazine hydrate with nitro ketene dithioacetal and its reaction with Knoevenagel adduct derived from the corresponding aldehyde and malononitrile in ethanol media. The formation of 5-membered pyrazole ring is confirmed based on the electrostatic surface potential computed by density functional theory. This strategy can provide a concise and eco-friendly route for easy access to the highly substituted pyrazoles derivatives in excellent yields using four simple and readily available building blocks under mild conditions and particularly attractive due to features such as atom economy, high yield and mild condition.

Synthesis of heterocyclic [3.3.3]propellanes via a sequential four-component reaction.

A highly chemoselective heteroannulation protocol for the synthesis of unreported polysubstituted heterocyclic [3.3.3]propellanes has been developed by sequential four-component reaction of ninhydrin, malononitrile, primary amines, and dialkyl acetylenedicarboxylates under mild conditions in water. To the best of our knowledge, there are no previous reports for the synthesis of these classes of heterocyclic [3.3.3]propellanes. The merit of this sequential Knoevenagel condensation/enamine formation/Michael addition/cyclization sequence is highlighted by its high atom-economy, excellent yields, the use of water as reaction media, and the efficiency of production without the use of any activator or metal promoters. This synthesis serves as a nice addition to group-assistant-purification (GAP) chemistry in which purification via chromatography and recrystallization can be avoided, and the pure products were obtained simply by washing the crude products with 95% ethanol.