Unexpected regio- and stereoselective [4 + 3] cycloaddition reaction of azomethine ylides with benzylidene thiazolidinediones: synthesis of pharmacologically active spiroindoline oxazepine derivatives and theoretical study

An unexpected regio- and stereoselective [4 + 3] cycloaddition reaction of azomethine ylides with 5-benzylidenethiazolidine-2,4-diones has been successfully developed for the synthesis of the novel pharmacologically active 4′,5′-dihydro-3′H-spiro[indoline-3,2′-[1, 3] oxazepin]-2-one derivatives in b...

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Bibliographic Details
Published in:Molecular diversity 2021-02, Vol.25 (1), p.29-43
Main Authors: Zahedifar, Mahboobeh, Pouramiri, Behjat, Ezzati Ghadi, Fereshteh, Razavi, Razieh, Ramzani Ghara, Abdollah
Format: Article
Language:English
Subjects:
Acids
Biochemistry
Biomedical and Life Sciences
Chemical reactions
Life Sciences
NMR
Nuclear magnetic resonance
Organic Chemistry
Original Article
Pharmacy
Polymer Sciences
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Summary:An unexpected regio- and stereoselective [4 + 3] cycloaddition reaction of azomethine ylides with 5-benzylidenethiazolidine-2,4-diones has been successfully developed for the synthesis of the novel pharmacologically active 4′,5′-dihydro-3′H-spiro[indoline-3,2′-[1, 3] oxazepin]-2-one derivatives in basic condition. Easy purification, high yield, short experimental time and operational simplicity are specific advantages of this protocol. Furthermore, all the synthesized compounds have been evaluated for antioxidant and antibacterial activities. According to the results, most of the synthesized compounds exhibited DPPH radical scavenging activity and nine of them showed antibacterial properties. The reaction mechanism and 1 H NMR spectrum have been evaluated by B3LYP/6311G method. Graphic abstract
ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-019-10022-z