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A Mild Method for the Synthesis of Carbamate-Protected Guanidines Using the Burgess Reagent

Toshikatsu Maki*, Takayuki Tsuritani and Tatsuro Yasukata

*Chemical Development Center, CMC Development Laboratories, Shionogi & Co., Ltd., 3-1-1, Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan, Email: toshikatsu.makishionogi.co.jp

T. Maki, T. Tsuritani, T. Yasukata, Org. Lett., 2014, 16, 1868-1871.

DOI: 10.1021/ol5002208 (free Supporting Information)



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Abstract

Various thioureas derived from primary amines and carbamoyl-protected isothiocyanates react with the Burgess reagent to give the corresponding guanidines via either a stepwise or one-pot procedure. A selective deprotection of the N,N′-diprotected guanidines affords N-monoprotected guanidines.

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Key Words

thioureas, guanidines, Cbz Group


ID: J54-Y2014