Synthesis of Five-Membered Cyclic Guanidines via Cascade [3 + 2] Cycloaddition of α-Haloamides with Organo-cyanamides

Chuan-Chuan Wang, Ya-Li Qu, Xue-Hua Liu, Zhi-Wei Ma, Bo Yang, Zhi-Jing Liu, Xiao-Pei Chen and Ya-Jing Chen*

*Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, Henan, China, Email: chenyjzzu.edu.cn

C.-C. Wang, Y.-L. Qu, X.-H. Liu, Z.-W. Ma, B. Yang, Z.-J. Liu, X.-P. Chen, Y.-J. Chen, J. Org. Chem., 2021, 86, 3546-3554.

DOI: 10.1021/acs.joc.0c02932

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Abstract

A cascade [3 + 2] cycloaddition between organo-cyanamides and α-haloamides provided N₂-unprotected five-membered cyclic guanidines under mild conditions in very good yields. The corresponding cyclic guanidines could be easily transformed into hydantoins via hydrolysis.

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Key Words

hydantoins

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ID: J42-Y2021