Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 6, Pages 1574-1579Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo01926k
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Funding
- Natural Science Foundation of Henan Province [212300410152]
- Key Scientific and Technological Project of Henan Province [212102110439]
- Henan University of Animal Husbandry and Economy [2019HNUAHEDF011, XKYCXJJ2020006]
- Key Scientific Research Project for Colleges and Universities of Henan Province [22B150005]
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A novel and efficient method for the synthesis of five-membered cyclic guanidines has been developed, which involves a regioselective ring-opening and cyclization process. The reaction proceeds under mild conditions without the need for metals or strong bases. Biologically active urea analogues can also be easily obtained through hydrolysis of the synthesized guanidines.
A novel and efficient [3 + 2] annulation of 2-substituted aziridines and N-tosyl cyanamides via a domino regioselective ring-opening/5-exo-dig cyclization procedure has been developed, allowing the direct preparation of N-2-unprotected five-membered cyclic guanidines in good to excellent yields under mild conditions without metals and strong bases. Moreover, the highly biologically interesting urea analogues could also be conveniently obtained via hydrolysis of the produced guanidines.
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