Unprecedented synthesis of indole-linked tetra-substituted alkenes by catalyst-free domino reaction

Abstract

Herein, we report a simple, efficient catalyst-free green domino reaction of indole, arylglyoxal, and cyclic 1,3-dicarbonyls such as barbituric acid derivatives/dimedone at 100oC in dimethylformamide medium in open air condition. In this reaction, one C-C and one C=C bonds have been formed in one-pot without using any additive or metal based reagent. Considering the presence of indole, benzoyl and cyclic 1,3-dicarbonyl moieties in the products, it is expected that they will exhibit interesting medicinal properties. All the synthesized products were characterized by recording FTIR, 1H NMR, 13C NMR, and HRMS. Moreover, a single crystal XRD of compound 4i was recorded to confirm the structure of the product. Operational simplicity, gram-scale synthesis, mild reaction conditions, good yields, and wide substrate scope are the salient features of this methodology.