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- Title
Chemoselective oxidation of 1-alkenylisatins with m-chloroperbenzoic acid. Synthesis of new derivatives of isatoic anhydride.
- Authors
Bogdanov, A.; Sadykov, T.; Musin, L.; Khamatgalimov, A.; Krivolapov, D.; Dobrynin, A.; Mironov, V.
- Abstract
Oxidation of alkyl- and alkenylisatins with m-chloroperbenzoic acid proceeds with high chemoselectivity leading to the formation of 1-substituted isatoic anhydrides (benzo[ d][1,3]oxazine-2,4-diones) without epoxidation of the double bond of the alkenyl substituent. This result is in accordance with the data of DFT quantum chemical calculations using the B3LYP functional in conjunction with the basis set of atomic orbitals 6-31G(d,p). The structure of the synthesized heterocyclic compounds was proved by NMR and X-ray diffraction data.
- Subjects
CHEMICAL reactions; OXIDATION; REACTIVITY (Chemistry); CHEMICAL kinetics; X-ray diffractometers
- Publication
Russian Journal of General Chemistry, 2015, Vol 85, Issue 9, p2030
- ISSN
1070-3632
- Publication type
Academic Journal
- DOI
10.1134/S1070363215090030