Soluble Polymer-Supported Synthesis of N,N-di(Boc)-Protected Guanidines

Jing-Ying Shey; Chung-Ming Sun

doi:10.1055/s-1998-1989

Synlett 1998; 1998(12): 1423-1425
DOI: 10.1055/s-1998-1989

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Soluble Polymer-Supported Synthesis of N,N-di(Boc)-Protected Guanidines

Jing-Ying Shey^* , Chung-Ming Sun

^*Department of Chemistry, National Dong Hwa University, Shou-Feng, Hualien 974, Taiwan; Fax (886)-3-8 66 14 87; E-mail: cmsun@cc.ndhu.edu.tw

Abstract

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A novel method for soluble, inexpensive polymer-supported synthesis of internal guanidines with piperazine and piperidine scaffolds has been developed. We carried out a preliminary study on the reactivity of N,N-bis-Boc-1-guanylpyrazole 1, N,N-bis-Boc-thiourea 2 and N,N-di-(tert-butoxycarbonyl)-S-methylisothiourea 3 with resin bound diamines in liquid phase. Guanidines are liberated from the polymer support in high yields and good purity by simple precipitation and washing. This liquid-phase method proves to be a useful tool for constructing guanidine libraries containing a diamine moiety.

guanidine - combinatorial chemistry - liquid-phase method - solid-phase method - scaffold

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