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Oxidative Aminoaziridination of 2‐Vinylfuran Derivatives as an Approach to Hexa‐2,5‐diene‐1,4‐dione Monohydrazones
Author(s) -
Sorokina Mariia V.,
Pankova Alena S.,
Kuznetsov Mikhail A.
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500460
Subject(s) - chemistry , hexa , diene , bicyclic molecule , furan , stereoselectivity , oxidative phosphorylation , stereochemistry , medicinal chemistry , organic chemistry , catalysis , natural rubber , biochemistry
The oxidative addition of N ‐aminophthalimide to substituted 2‐vinylfurans provides monophthaloylhydrazones of (2 Z )‐hexa‐2,5‐diene‐1,4‐dione derivatives instead of 2‐furylaziridines by proceeding through an aziridination of the endocyclic furan C=C bond followed by a regio‐ and stereoselective rearrangement of the bicyclic intermediate. The formation of stable aziridines can then occur through the aziridination of the ( E )‐C=C bond of these phthaloylhydrazones. Detailed structure elucidations and mechanistic considerations are provided.