Tertiary Amine-Catalyzed Stereoretentive Multi-Component Cascade Reaction of Carboxylic Acids: Facile Synthesis of Cyclic Ureas/Urethanes

Yi Hu; Yifei Cai; Yanfei Liu; Dan Xiong; Hui Yao; Linxuan Li; Zhong-Yan Cao; Nianyu Huang; Nengzhong Wang

doi:10.1002/cjoc.70110

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (17) : 2181 -2186. DOI: 10.1002/cjoc.70110

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Tertiary Amine-Catalyzed Stereoretentive Multi-Component Cascade Reaction of Carboxylic Acids: Facile Synthesis of Cyclic Ureas/Urethanes

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Abstract

Herein, we developed a tertiary amine-catalyzed stereoretentive multi-component cascade reaction featuring an amidation/[4 + 1] annulation/decarboxylation/Curtius rearrangement/[2 + n] annulation sequence. This metal-free and step-economic method provided a broad range of cyclic ureas/urethanes in green solvent under mild conditions without employing explosive and toxic reagents. Importantly, this reaction generated isocyanates in situ under catalytic conditions via a decarboxylation/Curtius rearrangement process of dioxazolones.

Keywords

Tertiary amine catalysis / Multi-component reaction / Annulation / Decarboxylation / Curtius rearrangement / Stereoretention / Carboxylic acids / Cyclic ureas / Cyclic urethanes / Synthetic methods / Organocatalysis / Michael addition

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Yi Hu, Yifei Cai, Yanfei Liu, Dan Xiong, Hui Yao, Linxuan Li, Zhong-Yan Cao, Nianyu Huang, Nengzhong Wang. Tertiary Amine-Catalyzed Stereoretentive Multi-Component Cascade Reaction of Carboxylic Acids: Facile Synthesis of Cyclic Ureas/Urethanes. Chinese Journal of Chemistry, 2025, 43(17): 2181-2186 DOI:10.1002/cjoc.70110