Camphor sulfonic acid catalyzed one-pot pseudo three-component synthesis of a series of 1,8-dioxo-octahydroxanthenes and comparative crystal structures investigations and Hirshfeld surface analysis of five such derivatives

A simple and convenient protocol has been developed for the synthesis of 1,8-dioxo-octahydroxanthenes via one-pot pseudo three-component reactions between two equivalents of dimedone and one-equivalent of aromatic aldehydes in the presence of a catalytic amount of camphor sulfonic acid as an efficient organocatalyst in ethanol under refluxed conditions. A variety of aryl as well as heteroaryl aldehydes were employed and all those afforded excellent yields of the desired products. The synthesized products were isolated pure in excellent yields by simple crystallization techniques. Use of organocatalyst, simple work up procedure, high atom economy, multicomponent strategy, easy isolation procedure and excellent yields are some of the major advantages of this newly developed protocol. X-ray crystallographic data of the five such synthesized 1,8-dioxo-octahydroxanthene derivatives were also recorded. 3D Hirshfeld surfaces and allied 2D fingerprint plots of these five 1,8-dioxo-octahydroxanthene derivatives were also analyzed further for molecular interactions.

Automated summary

A simple and convenient protocol for the synthesis of 1,8-dioxo-octahydroxanthenes has been developed using a one-pot pseudo three-component reaction. The reaction involves dimedone, aromatic aldehydes, and camphor sulfonic acid as a catalyst. The method offers advantages such as the use of an organocatalyst, simple work up procedure, high atom economy, multicomponent strategy, and easy isolation procedure.