Tsybulin, Semyon V. and Meshalkin, Stepan A. and Tonkoglazova, Daria I. and Bardakov, Victor G. and Pozharskii, Alexander F. and Antonov, Alexander S. (2025) A Precise Synthetic Toolbox: H-Bond-Assisted Quadruple Reactivity of o-Dimethylaminoaryloximes. JOURNAL OF ORGANIC CHEMISTRY, 90 (12). pp. 4374-4381. ISSN 0022-3263, 1520-6904
Full text not available from this repository. (Request a copy)Abstract
Non-covalent interactions are a highly promising tool for the development of transition-metal-free chemospecific synthetic transformations. Here, we demonstrate the implementation of non-covalent interactions as a simple, precise, and flexible synthetic toolbox, allowing the controlled transformation of o-dimethylaminoaryloximes into nitriles and hard-to-reach nitrogen heterocycles under mild conditions. This diverse reactivity is activated via hydrogen bonding and facilitated via the "buttressing effect" of the substituents next to the NMe2 group. All transformations require only simple and easily available acids and solvents, which generally provide precise control over the direction of the reaction, allowing the selective synthesis of nitriles, fused pyrazoles, isoxazoles, and pyrroles.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | OXIMES; HETEROCYCLES; BASICITY; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 23 Jun 2026 09:39 |
| Last Modified: | 23 Jun 2026 09:39 |
| URI: | https://pred.uni-regensburg.de/id/eprint/66447 |
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