One-pot synthesis of 2-oxa-7-azaspiro[4.4]nonane-8,9-diones using Mn(III)-based oxidation of 4-acylpyrrolidine-2,3-diones

[Display omitted] •A straightforward route to access the new 2-oxa-7-azaspiro[4.4]nonane-8,9-diones was found.•The structure of the 2-oxa-7-azaspiro products was well characterized by NMR and X-ray.•The mechanism for the formation of the products was proposed. 2-Oxa-7-azaspiro[4.4]nonane-8,9-diones...

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Bibliographic Details
Published in:Tetrahedron letters 2017-09, Vol.58 (37), p.3619-3622
Main Authors: Huynh, Thanh-Truc, Nguyen, Van-Ha, Nishino, Hiroshi
Format: Article
Language:English
Subjects:
1,1-Diarylethenes
4-Acylpyrrolidine-2,3-diones
Cycloaddition
Manganese(III) acetate
Oxaazaspiro[4.4]nonanedione
Oxidation
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Summary:[Display omitted] •A straightforward route to access the new 2-oxa-7-azaspiro[4.4]nonane-8,9-diones was found.•The structure of the 2-oxa-7-azaspiro products was well characterized by NMR and X-ray.•The mechanism for the formation of the products was proposed. 2-Oxa-7-azaspiro[4.4]nonane-8,9-diones were newly synthesized in good yields by the Mn(III)-based reaction of a mixture of 1,1-diarylethenes and 4-acylpyrrolidine-2,3-diones. Under the stated reaction conditions, the pyrrolidinedione ring remained intact and became one of the two rings of the 2-oxa-7-azaspiro[4.4]nonanedione scaffold. The procedure was simple and the product was easily separated. The structure determination and the mechanism for the formation of the 2-oxa-7-azaspiro[4.4]nonanediones were also discussed.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2017.08.002