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Synthesis of imino ethers (imidates)

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Pinner Reaction


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2,2,2-Trifluoro- and trichloroethyl imidates, which are easily prepared by reaction of a nitrile and a trihaloethanol in the presence of HCl, are excellent reagents for the preparation of amidines under mild reaction conditions.
S. Caron, L. Wei, J. Douville, A. Ghosh, J. Org. Chem., 2010, 75, 945-947.


A mild, one-pot cyanoimidation of aldehydes using cyanamide as a nitrogen source and NBS as an oxidant was achieved in high yields without the addition of a catalyst. Subsequently, the substituted N-cyanobenzimidate products may also undergo a cyclization reaction to give 1,2,4-triazole derivatives in high yields.
P. Yin, W.-B. Ma, Y. Chen, W.-C. Huang, Y. Deng, L. He, Org. Lett., 2009, 11, 5482-5485.


A N-trifluoromethylation of nitriles with PhICF3Cl followed by DMAP-catalyzed capture with N-, O-, or S-centered nucleophiles enables an efficient synthesis of a wide range of N-CF3 amidines, imidates, and thioimidates.
R. Z. Zhang, W. Huang, R. X. Zhang, C. Xu, M. Wang, J. Sun, Org. Lett., 2022, 24, 2393-2398.