引用本文:
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
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
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
A facile synthesis of imino-protected cyclic guanidine derivatives from diamines
摘要:
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.
English
A facile synthesis of imino-protected cyclic guanidine derivatives from diamines
Abstract:
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.
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Key words:
- Intramolecular cyclization
- / 1,4-Nucleophilic addition
- / Alkyldiamines
- / Cyclic guanidine
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