Synthesis of 4-(imidazolidin-2-ylidene(nitro)methyl)-2-oxo-2H-chromene-3-carbonitrile via a One-Pot, Three-Component Reaction

Heterocyclic ketene aminals (HKAs) are powerful and versatile intermediates in heterocyclic synthesis. The reactions of cyclic ketene aminals with a number of electrophilic reagents have been successfully used to synthesis five- and six-membered and fused heterocycles in recent years [1]. Coumarin moieties are a large group of oxygen-containing heterocycles that are widely distributed in plants such as grasses, legumes, and fruits. Coumarins possess a wide range of biological activities including anticoagulant, inhibition of HIV-1 protease [2]. Herein, We report the synthesis of coumarin-bearing nitroketeneaminal derivatives by reaction of salicylaldehydes (1), alkyl cyanoacetate (2), diamines, and 1,1- bis(methylsulfanyl)-2-nitroethene in EtOH. The reactions of salicylaldehydes (1), alkyl cyanoacetate(2), diamines and 1,1-bis(methylsulfanyl)-2-nitroethene were performed within 3 h in EtOH to produce the targetderivatives 3 in excellent yields(Figure 1). Easy performance highly functionalized in the molecule, good yields, and easy purification are the main advantages of this method. The structures were confirmed by IR, MS, 1H- and 13C-NMR analyses.