88064-00-0Relevant academic research and scientific papers
New Synthetic Applications of Aryllead Triacetates. N-Arylation of Azoles
Lopez-Alvarado, Pilar,Avendano, Carmen,Menendez, J. Carlos
, p. 5678 - 5682 (2007/10/03)
Treatment of a variety of azoles or their anions with p-tolyllead triacetate in the presence of copper(II) acetate afforded the corresponding N-aryl derivatives, normally in excellent yields.Room temperature arylation of an aminobenzimidazole derivative was chemoselectively directed to the amino group.
Benzotriazol-1-ylmethylammonium Salts Synthesis and Reactivity
Katritzky, Alan R.,Hughes, Craig V.,Rachwal, Stanislaw
, p. 1579 - 1588 (2007/10/02)
Benzotriazol-1-ylmethylamines on treatment with alkylating agents afford benzotriazol-1-ylmethylammonium salts, also available from reactions of chloromethylbenzotriazole with tertiary amines.In deuterated solvents under basic conditions the methylene protons of these salts exchange with deuterium.At elevated temperatures, an alkyl group substituent migrated from the ammonium center to the benzotriazolyl N-3.Reactions of the salts with Grignard reagents afforded various products arising from substitution of the ammonium moiety and/or from attack on the benzotriazolyl N-3 or on the benzenoid ring.
Reactions of 1-(α-Alkoxyalkyl)- and 1-(α-(Aryloxy)alkyl)benzotriazoles with the Grignard Reagents. A New and Versatile Method for the Preparation of Ethers
Katritzky, Alan R.,Rachwal, Stanislaw,Rachwal, Bogumila
, p. 6022 - 6029 (2007/10/02)
1-(α-Alkoxyalkyl)benzotriazoles deriving from aldehydes (other than formaldehyde), or from ketones, react with Grignard reagents at 110 deg C to provide a high-yielding, general synthesis of dialkyl and aryl ethers.Under similar conditions, 1-(alkoxymethyl)- and 1-((aryloxy)methyl)benzotriazoles give, by a different cleavage pattern of the N-C-O grouping, 1-alkylbenzotriazoles and N,N'-dialkyl-o-phenylenediamines.The 1-(α-alkoxyalkyl)benzotriazoles are easily prepared: (a) by condensation of benzotriazole, an aldehyde, and an alcohol under water-removing conditions; (b) by condensation of a 1-(α-chloroalkyl)benzotriazole with a sodium or potassium alkoxide or aryloxide; and (c) by condensatioon of an acetal or a ketal with benzotriazole.All the 1-(α-alkoxyalkyl)benzotriazoles and dialkyl or alkyl aryl ethers obtained were fully characterized by their 1H and 13C NMR spectra.
The Chemistry of N-Substituted Benzotriazoles. Part 1. 1-(Chloromethyl)-benzotriazole
Katritzky, Alan R.,Rachwal, Stanislaw,Caster, Kenneth C.,Mahni, Fatma,Law, Kam Wah,Rubio, Olga
, p. 781 - 790 (2007/10/02)
The N-chloromethyl group of 1-(chloromethyl)benzotriazole undergoes nucleophilic substitution by carbon, nitrogen, phosphorus, oxygen, and sulphur nucleophiles. α-Lithiation was achieved in high yield in 1-phenylthiomethyl-, 1-phenylsulphinylmethyl-, and 1-(phenylsulphonylmethyl)benzotriazoles and the lithio derivatives reacted with a variety of electrophiles.New benzotriazolium salts were prepared by quaternization of the N-3 nitrogen with methyl iodide.
