189343-70-2Relevant academic research and scientific papers
Iodine-induced regioselective direct alkylation of azoles via in situ formed alkyliodide
Chen, Wenlin,Yan, Rulong,Tang, Dong,Guo, Shuaibo,Meng, Xu,Chen, Baohua
supporting information; experimental part, p. 7956 - 7959 (2012/09/21)
We have developed an efficient, metal-free, convenient and relatively cheap method for iodine-induced direct alkylation of azoles via in situ formed alkyliodide. A series of heterocyclic derivatives are readily prepared under mild conditions in moderate t
Gas-phase thermolysis of benzotriazole derivatives: Part 1 - Synthesis of α-N(1)- and N(2)-benzotriazolyl ketones and kinetics and mechanism of their gas-phase pyrolysis
Dib, Hicham H.,Al-Awadi, Nouria A.,Ibrahim, Yehia A.,El-Dusouqui, Osman M.E.
, p. 267 - 272 (2007/10/03)
1-(Benzotriazol-1-yl)propan-2-one (1) and 3-(benzotriazol-1-yl)butan-2-one (2), and their respective phenyl analogues 2-(benzotriazol-1-yl)-1- phenylethanone (3) and 2-(benzotriazol-1-yl)-1-phenylpropan-1-one (4), together with 1-cyanobenzotriazole (5) and 1-(benzotriazol-2-yl)propan-2-one (6), were synthesized and then subjected to gas-phase thermolysis. The products of complete pyrolysis of 1-4 were found to be aniline in addition to either 2-substituted indoles or 2,3-disubstituted indoles. The kinetics of the gas-phase thermal elimination reactions of the present compounds were also studied, the first such investigation on benzotriazoles. The Arrhenius preexponential factor (A/s-1) and activation energy (Ea/kJ mol-1) are, respectively: 10.03 and 156.7 for (1), 9.93 and 158.0 for (2), 12.68 and 169.9 for (3), 9.45 and 144.4 for (4) and 15.40 and 163.6 for (5). Compound 6 appeared to have isomerized by a thermally allowed 1,5-group migration into 1 prior to thermolysis. The results of the kinetic and product analysis are rationalized with reference to a mechanism involving extrusion of a stable (N2) molecule and formation of a reactive 1,3-biradical intermediate, which in turn rearranges into the final products of reaction. 2004 John Wiley & Sons, Ltd.
A Novel Transformation of Esters to Alkynes with 1-Substituted Benzotriazoles
Katritzky, Alan R.,Wang, Jin,Karodia, Nazira,Li, Jianqing
, p. 4142 - 4147 (2007/10/03)
Reactions of lithio benzotriazol-1-yl derivatives 2, 11, and 25 with aromatic and aliphatic esters 3, 12, and 26 gave α-(benzotriazol-l-yl) ketones 4, 13, and 27, respectively, in high yields. Alternatively, α-(benzotriazol-l-yl) ketones 22 can be accessed by the reaction of α-(benzotriazol-1-yl) esters 20 with Grignard reagents. Condensation of 4, 13, 22, and 27 with (p-toluenesulfonyl)hydrazine provided p-tosylhydrazones 5, 14, 21, and 28. Treatment of hydrazones 5, 21, and 28 with n-butyllithium in diethyl ether resulted in the elimination of the tosyl group, dinitrogen, and benzotriazolyl group to afford the corresponding acetylenes 9, 23, and 29 in good yields. When α-(benzotriazol-l-yl) 1-α-phenoxy hydrazones 14 were treated with methyllithium, n-butyllithium, or phenyllithium, alkynes 18 were obtained, in which phenoxy groups were replaced by the lithium reagents.
