Categories: C-N Bond Formation >
Synthesis of guanidines
Related: |
 |
 |
Recent Literature
A modified Ullmann reaction allows the use of p-methoxybenzyl (PMB)
guanidine as guanidinylation agent to give various aryl and heteroaryl
guanidines in good yields.
H. Hammoud, M. Schmitt, F. Bihel, C. Antheaume, J.-J. Bourguignon, J. Org. Chem., 2012,
77, 417-423.
An operationally simple and rapid copper-catalyzed three-component synthesis of
trisubstituted N-aryl guanidines involving cyanamides, arylboronic acids,
and amines is performed in the presence of K2CO3, a
catalytic amount of CuCl2·2H2O, bipyridine, and oxygen (1
atm).
J. Li, L. Neuville, Org. Lett., 2013,
15, 6124-6127.
Palladium-catalyzed alkene carboamination reactions between acyclic N-allyl
guanidines and aryl or alkenyl halides provide substituted 5-membered cyclic
guanidines in good yield. This method allows access to a number of different
cyclic guanidine derivatives in only two steps from readily available allylic
amines.
B. P. Zavesky, N. R. Babij, J. A. Fritz, J. P. Wolfe, Org. Lett., 2013,
15, 5420-5423.
A silver-catalyzed hydroamination of tosyl-protected N-allylguanidines
provides substituted cyclic guanidines in high yields. The reactions can be used
for construction of quaternary stereocenters as well as both monocyclic and
bicyclic guanidine products.
Z. J. Garlets, M. Silvi, J. P. Wolfe, Org. Lett.,
2016, 18, 2331-2334.
A novel electrophilic one-pot reaction of an olefin, a cyanimide, an
amine, and N-bromosuccinimide enables the synthesis of a number of
guanidine derivatives with very good yields - including an rTRTVI precursor.
L. Zhou, J. Chen, J. Zhou, Y.-Y. Yeung, Org. Lett., 2011,
13, 5804-5807.