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Synthesis of guanidines

Recent Literature


Simple lanthanide amides are highly efficient catalysts for the guanylation of both aromatic and secondary amines with a high activity under mild conditions. These catalysts are compatible with a wide range of solvents and substrates.
Q. Li, S. Wang, S. Zhou, G. Yang, X. Zhu, Y. Liu, J. Org. Chem., 2007, 72, 6763-6767.


Q. Li, S. Wang, S. Zhou, G. Yang, X. Zhu, Y. Liu, J. Org. Chem., 2007, 72, 6763-6767.


Two new guanidinylation reagents, N,N′-bis(ortho-chloro-Cbz)-S-methylisothiourea and N,N′-bis(ortho-bromo-Cbz)-S-methylisothiourea, proved to be superior to already known reagents. The guanidinylations of amines with all reagents were accelerated by addition of DMAP.
T. Gers, D. Kunce, P. Markowski, J. Izdebski, Synthesis, 2003, 37-42.


A convenient one-step transformation of primary and secondary amines into the corresponding unprotected guanidines using 4-benzyl-3,5-dimethyl-1H-pyrazole-1-carboxamidine and its polymer-bound variant is described. The scopes and limitations of the method, the microwave-assistance of amidination as well as a recycling protocol are examined.
W. Solodenko, P. Bröker, J. Messinger, U. Schön, A. Kirschning, Synthesis, 2006, 461-466.


The synthesis of 3,5-dimethyl-N-nitro-1-pyrazole-1-carboxamidine (DMNPC) has been optimised. A detailed protocol for the preparation of a range of guanidines via nitroguanidines is described using DMNPC as guanidinylating reagent.
J. A. Castillo-Meléndez, B. T. Golding, Synthesis, 2004, 1655-1663.


Primary amines are converted to protected NG-hydroxyguanidines in a one-pot procedure using readily prepared materials. A high-yielding preparation of NG-hydroxy-L-arginine, the intermediate in the enzymatic conversion of L-arginine to nitric oxide and L-citrulline by nitric oxide synthase, is described.
N. I. Martin, J. J. Woodward, M. A. Marletta, Org. Lett., 2006, 8, 4035-4038.