biostudies-literatureSingh MKDivision of ChemistryNIMHD NIH HHSNational Institute on Minority Health and Health Disparities1921-1928https://www.ebi.ac.uk/biostudies/studies/S-EPMC4993530biostudies-literatureUnknown6(3)C(sp³)-N bond-forming reactions between benzotriazole and 5,6-dimethylbenzotriazole with <i>N</i>-methylpyrrolidinone, tetrahydrofuran, tetrahydropyran, diethyl ether, 1,4-dioxane, and isochroman have been conducted using RuCl₃•3H₂O/<i>t</i>-BuOOH in 1,2-dichloroethane. In all cases, <i>N</i>1 and <i>N</i>2 alkylation products were obtained, and these are readily separated by chromatography. One of these products, 1-(isochroman-1-yl)-5,6-dimethyl-1<i>H</i>-benzotriazole, was examined by X-ray crystallography. It is the first such compound to be analyzed by this method, and notably, the benzotriazolyl moiety is quasi-axially disposed, consistent with the anomeric effect. This has plausible consequences, not observed previously. In contrast to other hemiaminaACS catalysisRuthenium-Catalyzed C-H Bond Activation Approach to Azolyl Aminals and Hemiaminal Ethers, Mechanistic Evaluations, and Isomer Interconversion.PMC4993530G12MD007603CHE-1265687G12 MD007603Lakshman MKSingh MKSatishkumar SAkula HKStahl LfalseRuthenium-Catalyzed C-H Bond Activation Approach to Azolyl Aminals and Hemiaminal Ethers, Mechanistic Evaluations, and Isomer Interconversion.C(sp³)-N bond-forming reactions between benzotriazole and 5,6-dimethylbenzotriazole with <i>N</i>-methylpyrrolidinone, tetrahydrofuran, tetrahydropyran, diethyl ether, 1,4-dioxane, and isochroman have been conducted using RuCl₃•3H₂O/<i>t</i>-BuOOH in 1,2-dichloroethane. In all cases, <i>N</i>1 and <i>N</i>2 alkylation products were obtained, and these are readily separated by chromatography. One of these products, 1-(isochroman-1-yl)-5,6-dimethyl-1<i>H</i>-benzotriazole, was examined by X-ray crystallography. It is the first such compound to be analyzed by this method, and notably, the benzotriazolyl moiety is quasi-axially disposed, consistent with the anomeric effect. This has plausible consequences, not observed previously. In contrast to other hemiamina2016-01-01T00:00:00Z2016 Mar2025-04-18T18:09:56.174Z2019-03-27T02:21:13ZS-EPMC49935302756349210.1021/acscatal.5b02603