Chemoselective oxidation of 1-alkenylisatins with m-chloroperbenzoic acid. Synthesis of new derivatives of isatoic anhydride.

Bogdanov, A.; Sadykov, T.; Musin, L.; Khamatgalimov, A.; Krivolapov, D.; Dobrynin, A.; Mironov, V.

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.

CHEMICAL reactions; OXIDATION; REACTIVITY (Chemistry); CHEMICAL kinetics; X-ray diffractometers

Russian Journal of General Chemistry, 2015, Vol 85, Issue 9, p2030

1070-3632

Academic Journal

10.1134/S1070363215090030