Journal
CURRENT ORGANIC SYNTHESIS
Volume 15, Issue 3, Pages 404-413Publisher
BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/1570179414666170830124447
Keywords
4-Aryl-4-oxo-but-2-enoic acid; furanone; spiropyrimidone; pyridazin-3-one; spiropyrazole; 1,2-oxazinone
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Funding
- Science and Technology Development Fund of Egypt (STDF)
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Background: The regioselective synthesis of spiro-heterocyclic compounds is intriguing since those compounds have unique non-planar structures and great potential for binding to biomolecules because of their inherent rigid chiral structure. A novel class of furanone and spiro-heterocyclic derivatives were synthesized and evaluated for antifungal activities to establish structure-activity relationship (SAR). Results: The synthesis was carried out through one-pot multicomponent reaction (MCR) of 4-aryl-4-oxo-2-butenoic acids, camphor, urea, and hydrogen peroxide in the presence of sodium ethoxide as a catalyst using a microwave irradiation method and / or a traditional thermal method. They are used as key starting materials to synthesize some heterocyclic compounds. Structures of all synthesized compounds were elucidated by elemental analyses and spectroscopic data. Conclusion: A facile and efficient method for the preparation of a new furanone, chalcone and spiropyrimidone derivatives via the one-pot MCR with the microwave-assisted irradiation was established.
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