Diversity-oriented catalyst-free synthesis of pseudopeptides containing rhodanine scaffolds via a one-pot sequential isocyanide-based six-component reactions in water using ultrasound irradiation

A planning strategy for diversity-oriented catalyst-free synthesis of pseudopeptides containing rhodanine scaffolds has been developed via a novel one-pot sequential six-component reaction in water. This approach is an efficient, environmentally friendly and expeditious procedure for direct access to wide ranges of pharmacologically significant and structurally interesting compounds based on the union of multicomponent reactions approach via tandem Michael/domino cycloaddition/Ugi reactions sequence from readily available starting materials. The syntheses were achieved by reaction of various primary amines, carbon disulfide, maleic anhydride or itaconic anhydride, aromatic aldehydes, anilines and isocyanides under ultrasound irradiation at room temperature in good yields. Providing of pseudopeptides containing rhodanines with the tandem formation of one new heterocyclic ring as well as creating the seven new bonds such as carbon-carbon, carbon-nitrogen, carbon-oxygen and carbon-sulfur with great efficiency and high atom/bond-forming/structure economy are outstanding features of this designed synthetic route.