Zr(HSO4)4: Green, efficient and reusable catalyst for one-pot synthesis of 1,8-dioxooctahydroxanthene under solvent-free conditions

Abstract

Many methods have been used to synthesize xanthene derivatives using different catalysts. However, some of these methodologies have not been entirely satisfactory. Most of the mentioned methods have disadvantages such as low yields, prolonged reaction times, harsh reaction conditions and the requirement of expensive catalysis and use of toxic organic solvent. In this research, a green and highly efficient procedure for the one-pot synthesis of 1,8-dioxo-octahydro-xanthenes has been developed. Zr(HSO4)4 catalyst was used as an efficient and recoverable catalyst for synthesis of 1,8-dioxo-octahydro-xanthene derivatives via cyclocondensation of dimedone and aromatic aldehydes in solvent-free conditions. There are no examples of the use of Zr(HSO4)4 for the synthesis of 1,8-dioxo-octahydro-xanthene derivatives. The present method offers several advantages such as green, highly efficient, recoverable, reusable, simple work-up and simple purification of products. The structure of the synthesized products was confirmed by Fourier Transform Infrared (Ft-IR) and Proton nuclear magnetic resonance (1HNMR) analyzes. The antibacterial activity of the synthesized compounds was determined by agar disk diffusion method against gram-positive (S. aureus bacteria) and gram-negative (E. coli bacteria) microorganisms. Among the synthesized compounds (3a-3j), 3h compound showed the highest antibacterial effect by forming an inhibitory diameter zone of 15 mm around the disc containing 2000 mg of 3h-compound against gram-positive (S. aureus bacteria).1. Use of Zr(HSO4)4 as a green and highly efficient and reusable heterogeneous catalyst.2. Under solvent-free condition.3. Simple work-up and Simple purification of products.