Synthesis of Imidazolidinone-Fused 3,1-Benzoxazines via One-Pot Multicomponent Reactions
Zilong Tang1, Hongjuan Chen1, Yuhua Tan1
1Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of the Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201, China.
Abstract:
A novel palladium-catalyzed one-pot multicomponent reaction has been developed for the efficient synthesis of imidazolidinone-fused 3,1-benzoxazine derivatives from simple and readily available starting materials, including 2-aminoarylmethyl alcohols, ethyl glyoxylate, and amines. Notably, this transformation proceeds under mild conditions with a broad substrate scope, high trans-selectivity, and operational simplicity. The method enables the efficient construction of five new bonds and two ring moieties in one pot process, offering straightforward access to structurally diverse polycyclic fused 3,1-benzoxazine derivatives. Density functional theory (DFT) calculations were employed to elucidate the reaction mechanism and rationalize the observed trans-selectivity. Preliminary biological evaluations revealed promising antifungal activity in selected derivatives.
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