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

The convenient preparation of N2-unprotected five-membered cyclic guanidines was achieved through a cascade [3 + 2] cycloaddition between organo-cyanamides and α-haloamides under mild conditions in good to excellent yields (up to 99%). The corresponding cyclic guanidines could be easily transformed into hydantoins via hydrolysis.

Citation

Chuan-Chuan Wang, Ya-Li Qu, Xue-Hua Liu, Zhi-Wei Ma, Bo Yang, Zhi-Jing Liu, Xiao-Pei Chen, Ya-Jing Chen. Synthesis of Five-Membered Cyclic Guanidines via Cascade [3 + 2] Cycloaddition of α-Haloamides with Organo-cyanamides. The Journal of organic chemistry. 2021 Feb 19;86(4):3546-3554

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PMID: 33538590

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