Organic Chemistry Portal
Reactions > Organic Synthesis Search

Categories: C=N Bond Formation >

Synthesis of guanidines


Recent Literature

An efficient Pd-catalyzed cascade reaction of azides with isonitriles and amines provides N-sulfonyl-, N-phosphoryl-, and N-acyl-functionalized guanidines in excellent yield. In addition, the less reactive intermediate benzoyl carbodiimide could be isolated in moderate yield.
G. Qiao, Z. Zhang, B. Huang, L. Zhu, F. Xiao, Z. Zhang, Synthesis, 2018, 50, 330-340.

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