175351-38-9Relevant articles and documents
Reaction of imidazoles with cyanogen bromide: Cyanation at N 1 or bromination at C 2?
McCallum, Peter B.W.,Weavers, Rex T.,Grimmett, M. Ross,Blackman, Allan G.
, p. 159 - 165 (2007/10/03)
The reaction in acetonitrile solution of a number of imidazoles (1H-, 1-methyl-, 2-methyl-, 4-methyl-, 1,2-, 1,4- and 1,5-dimethyl-, 1-ethyl-, 1-benzyl- and 1-butyl-imidazole) and imidazole complexes ([Co(NH3)5(imH)](ClO4)3, [Co(NH3)5(im)] (ClO4)2 and [Co(NH3)5(1-Meim)] (ClO4)3) with BrCN has been studied. Those imidazoles bearing an N-alkyl substituent and having a hydrogen at C2 react to give the 2-bromo products, while the N-H imidazoles react to give W-cyano derivatives. The product(s) from the reaction of 1,2-dimethylimidazole with BrCN could not be characterized. Of the complexes, only [Co(NH3)5(im)] (ClO4)2 reacts, giving the 2-bromo product. Our observations suggest a lone pair on a ring nitrogen atom is necessary for an imidazole to react with BrCN, and a possible mechanism is suggested. The X-ray structure of 2-methylimidazole-1-carbonitrile is reported. Crystal data (-143°C) for C5H5N3: monoclinic, P21/c, a 10.201(5), b 7.110(3), c 7.227(3) A, β 100.47(2)°, V 515.4(4) A3, Z 4, dcalcd 1-380 g cm-3. Refinement of the structure converged with R1 0.0444 for 1183 reflections with Fo > 4F(Fo) and ωR2 0.1259 for all 1278 data.
Synthesis of N-Cyanoazoles
Purygin, P. P.,Pan'kov, S. V.
, p. 865 - 867 (2007/10/03)
1-Cyanoimidazole, 1-cyano-2-methylimidazole, 1-cyanobenzimidazole, and 1-cyano-1,2,4-triazole were prepared by reaction of corresponding azoles with cyanogen bromide.Reactions of cyanogen bromide with sodium benzotriazolide and sodium pyridin-2-olate yield 1-cyanobenzotriazole and 2-cyanatopyridine.
