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Current Organic Synthesis

Author(s): Fatemeh Ghorbani, Seied Ali Pourmousavi* and Hamzeh Kiyani

DOI: 10.2174/1570179417666200409144600

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Novel Biomass Derived from Grape Pomace Waste as an Efficient Nanocatalyst for the Synthesis of Dibenzoxanthene, Tetraketone, bis(indolyl)alkane and Chromene Derivatives and their Antimicrobial Evaluation

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Abstract

Background: Sulfonated carbon-based solid acids (CBSAs) have been reported as an efficient solid acid catalyst for many acid-catalyzed reactions. Furthermore, the use of carbon obtained from biomass waste has been explored and these materials showed a higher catalytic performance and higher stability compared to other solid acids.

Objective: Novel biomass carbon-based solid acids nanoparticles with high catalytic activity in organic transformation, such as Grape pomace waste-SO3H Nanoparticles (GPW-SO3H NPs), were successfully synthesized.

Materials and Methods: Grape pomace waste-SO3H Nanoparticles (GPW-SO3H NPs) were successfully synthesized. The grape pomace waste was dried in an oven at a temperature of 70°C and crushed to powder using an electric spice grinder. A mixture of powdered grape pomace waste (1 g) and concentrated sulfuric acid (>98%, 10 mL) was stirred at room temperature. Then, the resultant mixture was transferred into a 100 mL sealed Teflon-lined autoclave and kept at 180°C for 12 h. After cooling to room temperature, the resulting black solid was dried at 100°C in an oven under vacuum and the sulfonic acid-functionalized magnetic nanoparticles (Fe3O4@C-SO3H) were obtained.

Results and Discussions: The catalytic activity of GPW-SO3H was assessed through an easy and rapid protocol developed for the one-pot synthesis of 14-aryl-14-H-dibenzo [a,j]xanthene, arylmethylene [bis(3- hydroxy-2-cyclohexene-1-one)], bis(indolyl)alkane and 2-amino-4-aryl-7-hydroxy-4H-chromene-3-carbonitrile derivatives in excellent yields. The advantages of this method include use of waste material for catalyst synthesis, high yields, mild reaction conditions, uncomplicated work-up procedures, neutral conditions, and recoverable catalyst.

Conclusion: We have shown that biomass-derived solid acids, prepared from grape pomace waste, serve as a non-toxic, inexpensive and a promising eco-friendly and novel carbon-based solid acid nanocatalyst for organic transformations.

Keywords: Carbon-based solid acids, grape pomace waste, dibenzoxanthene, tetraketone, bis(indolyl)alkane, chromene.

Graphical Abstract

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