Abstract
An efficient, one-pot, two-step, four-component reaction for the synthesis of propellane derivatives is described by the condensation reaction between acenaphthenequinone, malono derivatives, primary amines and β-ketoester or β-diketone derivatives in the presence of triethylamine in ethanol at room temperature. Using this procedure, all the products were obtained in good to excellent yields.
Highlights
The design and application of multi-component reactions has attracted great attention from research groups working in areas such as biological, medicinal and organic chemistry
In continuation of our research on the synthesis of biologically important heterocycles and green chemistry protocols,[35–47] we report a simple and efficient method for the synthesis of novel propellane derivatives via a one-pot, sequential four-component condensation reaction between acenaphthoquinone (1), malono derivatives (2), primary amines (4) and b-ketoester or b-diketone (5) derivatives in the presence of triethylamine in ethanol at room temperature (Scheme 1)
High atom-economy, simple procedure in the excellent yields, easy workup procedure, mild reaction conditions and metalcatalyst free are the main advantages of this method
Summary
The improvement of reaction efficiency, the reduction of waste, the avoidance of toxic reagents and the responsible utilization of our resources have become critical objectives.[1,2] Multi-component reactions, are useful tools for the synthesis of biologically and pharmacologically important compounds because of their environmentally friendly, green characteristics and atom efficient.[3,4,5,6] the design and application of multi-component reactions has attracted great attention from research groups working in areas such as biological, medicinal and organic chemistry.Heterocyclic compounds occur commonly in nature and are essential to life.[7]. There have been some reports about the synthesis of propellane compounds from ninhydrin25–32 and acenaphthoquinone.32–34 In continuation of our research on the synthesis of biologically important heterocycles and green chemistry protocols,35–47 we report a simple and efficient method for the synthesis of novel propellane derivatives via a one-pot, sequential four-component condensation reaction between acenaphthoquinone (1), malono derivatives (2), primary amines (4) and b-ketoester or b-diketone (5) derivatives in the presence of triethylamine in ethanol at room temperature (Scheme 1).
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