Synthesis of guanidines

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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.

Guanidine cyclic diimide (GCDI) structures effectively destabilize the resonance structure of the guanidine group. In the presence of acid additives, the guanidine carbon center of GCDIs undergoes nucleophilic substitution reactions with various amines and alcohols.
T. An, Y. Lee, Org. Lett., 2021, 23, 9163-9167.