Categories: C=N Bond Formation >
Synthesis of amidines
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Recent Literature
The condensation of primary amine with N,N-dimethylacetamide dimethyl
acetal yields a mixture of acetamidine and imidate ester depending on the
temperature, solvent, and structure of the primary amine. It is possible to
suppress the formation of imidate ester by performing the reaction in the
presence of excess dimethyl amine, yielding acetamidine as the exclusive product.
J. R. Harjani, C. Liang, P. G. Jessop, J. Org. Chem., 2011,
76, 1683-1691.
The reaction of enamines with azides proceeds under catalyst-free conditions and
results in the formation of either sulfonyl amidine or β-amino sulfonyl enamine
derivative in good yields.
T. Gao, M. Zhao, X. Meng, C. Li, B. Chen, Synlett, 2011,
1281-1284.
The addition of amines to nitriles catalyzed by ytterbium amides gives
monosubstituted N-arylamidinates in good to excellent yields at 100°C
under solvent-free conditions.
J. Wang, F. Xu, Q. Shen, Org. Lett., 2008,
10, 445-448.
A highly efficient, mild, copper-catalyzed multicomponent reaction
for the synthesis of N-sulfonylamidines has been developed. This reaction has an
extremely wide scope with regard to all three coupling components of alkyne,
sulfonyl azide, and amine. Two plausible mechanistic pathways are discussed.
I. Bae, H. Han, S. Chang, J. Am. Chem. Soc.,
2005, 127, 2038-2039.
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