Citation: Jian Hai Yuan, Xiao Xiao Yang, Hao Lin, De Xin Wang. A facile synthesis of imino-protected cyclic guanidine derivatives from diamines[J]. Chinese Chemical Letters, ;2011, 22(12): 1399-1402. doi: 10.1016/j.cclet.2011.07.008 shu

A facile synthesis of imino-protected cyclic guanidine derivatives from diamines

Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

Received Date: 19 April 2011

Fund Project: We thank Project 81001366 supported by NSFC and basic scientific research foundation of Institute of Materia Medica (No.2009CHX07) for financial support.

A convenient one-step synthesis of five-membered or six-membered imino-protected cyclic guanidine via an intramolecular ring-closure reaction of alkyl diamine (2a-2g) with 1, 3-diamino-protected methylisothiourea (la and 1b) was established and investigated. Amino guanidine such as 3-(2-aminoethyl)-l, 2-dibenzyloxycarbonylguanidine (4a) has been proved to be the intermediate of the reaction via utilizing mono-protected diamine as starting material. The intramolecular ring closure of 4a results in 2-benzyloxycarbonyliminoimidazolidine (3a). This new one-step synthesis has advantages of simple condition, easy workup procedure and reasonable yield.
- Intramolecular cyclization,
- 1,4-Nucleophilic addition,
- Alkyldiamines,
- Cyclic guanidine
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