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Synthesis of unsymmetrical urea derivatives via one-pot sequential three-component reactions of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes

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Abstract

A novel and efficient multicomponent reaction of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes has been developed, and it leads to unsymmetrical urea derivatives with good yields in a single operation. This transformation involves the cascade formation of C–X (X = Cl, Br, I), C–N and C[double bond, length as m-dash]O bonds through halogenation, nucleophilic addition, ring-opening, and enol–ketone tautomerization processes. This protocol is step- and atom-economical; 1,2-dihaloethane was used as an easily available halogenated reagent, and it is amenable to different functional groups.

Graphical abstract: Synthesis of unsymmetrical urea derivatives via one-pot sequential three-component reactions of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes

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Article information


Submitted
01 Apr 2020
Accepted
18 May 2020
First published
19 May 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

Synthesis of unsymmetrical urea derivatives via one-pot sequential three-component reactions of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes

X. He, C. Yang, Y. Wu, M. Xie, R. Li, J. Duan and Y. Shang, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00683A

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