We present a two-step, general synthesis of N-arylputrescines and cadaverines, by cesium carbonate mediated alkylation of anilines with w-chloronitriles and subsequent reduction. The cesium-mediated alkylation shows remarkable selectivity towards the monoalkylation product. The method is straightforward and leads to satisfactory global yields.
Amines Q 0120An Efficient Synthesis of N-Arylputrescines and Cadaverines. -Title compounds (IV) are prepared via a two-step sequence involving alkylation of anilines with chloronitriles followed by reduction with BH3. -(LINK, N. P.; DIAZ, J. E.; ORELLI*, L. R.; Synlett 2009, 5, 751-754; Dep. Quim. Org., Fac. Farm. Bioquim., Univ. Buenos Aires, 1113 Buenos Aires, Argent.; Eng.) -Mais 32-065
We describe the synthesis of a series of 1-aryl-2,3-dialkyl-1,4,5,6-tetrahydropyrimidinium salts 1, by alkylation of the corresponding 1,4,5,6-tetrahydropyrimidines 2. We analyze the changes in the 1 H and 13 C NMR spectra of compounds 2 induced by protonation and quaternization. The results of an ab initio theoretical study on amidine 2a, and the cations resulting from its protonation (2aH + ) and quaternization (1a + ) are presented. A qualitative correlation was found between 13 C NMR and theoretical data in the case of protonation. The influence of the substitution patterns in the 1 H and 13 C NMR spectra of compounds 1 is also discussed.
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