Sustainable aqueous-mediated one-pot synthesis of 2-hydroxy-5-oxo-5,6,7,8-tetrahydro-4H-chromene and coumarin derivatives using taurine as the green bioorganic catalyst
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引用次数: 0
Abstract
In this study, two taurine-catalyzed, aqueous-mediated methodologies were reported for the synthesis of 4-aryl-2-hydroxy-7,7-dimethyl-5,6,7,8-tetrahydro-4H-chromen-5-one (3a-j) and 3-substituted coumarin derivatives (3′a-f) under reflux conditions. These methodologies entail the use of substituted aromatic aldehydes, diethyl malonate, and dimedone as reagents for the sustainable synthesis of 2-hydroxy-tetrahydro-4H-chromene derivatives via the Knoevenagel-Michael cascade, as well as the use of substituted salicylaldehyde with diethyl malonate or ethyl 3-oxobutanoate for the efficient synthesis of coumarin derivatives via the Knoevenagel-transesterification reaction. These strategies emphasize environmental sustainability and are designed as one-pot processes, ensuring simplicity and convenience. The methods deliver high yields and are cost-effective, significantly reducing reaction times, enhancing step efficiency, and are successful at the multigram level. Notably, the taurine catalyst demonstrates exceptional reusability, maintaining its activity for up to five cycles without notable degradation. The catalyst is easily recoverable through filtration, and the overall procedure is streamlined, requiring no additional purification steps. These attributes collectively contribute to the green chemistry paradigm by minimizing waste and energy consumption, thus offering a practical and efficient approach to the synthesis of these important organic compounds.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.