S. Medvedeva, Alexey V. Movchan, I. Zavarzin
Apr 23, 2022
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0
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1
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Journal
Arkivoc
Abstract
When various pyrrolo[3,2,1-ij ]quinoline-1,2-diones were oxidized with m -chloroperbenzoic acid, 1,3-oxazino[5,4,3 -ij ]quinolin-1,3-diones were obtained in good yields (64 – 86%) and characterized by spectral methods. Recyclization/rearrangement of the pyrroldione fragment of pyrrolo[3,2,1-ij ]quinoline-1,2-diones, regardless of the presence and electronic nature of the substituent in the aromatic part, the presence of a bulky phenyl group or a multiple bond in the heterocyclic fragment, proceeds selectively with the formation of a 1,3-oxazine cycle, rather than an isomeric 1,4-oxazine ring. This outcome corresponds to the data acquired from quantum mechanical calculations