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Synthesis of Cyanamides

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A novel and facile transformation of N,N-disubstituted glycylamides into corresponding cyanamides using pentavalent iodine reagents and tetraethylammonium bromide offers advantages such as use of non toxic reagents, shorter reaction times and good yields.
K. H. Chaudhari, U. S. Mahajan, D. S. Bhalerao, K. G. Akamanchi, Synlett, 2007, 2815-2818.


A low-temperature metalation of N-substituted 5H-tetrazoles followed by spontaneous cycloreversion at 0C provides N-metalated cyanamides that can be reacted in situ with a variety of electrophiles. Addition of lithium organometallics to the N,N'-disubstituted cyanamides enables the synthesis of N,N'-disubstituted amidines.
E. Duchamp, S. Hanessian, Org. Lett., 2020, 22, 8487-8491.


A low-temperature metalation of N-substituted 5H-tetrazoles followed by spontaneous cycloreversion at 0C provides N-metalated cyanamides that can be reacted in situ with a variety of electrophiles. Addition of lithium organometallics to the N,N'-disubstituted cyanamides enables the synthesis of N,N'-disubstituted amidines.
E. Duchamp, S. Hanessian, Org. Lett., 2020, 22, 8487-8491.