Please use this identifier to cite or link to this item: http://hdl.handle.net/11452/22995
Title: Cycloaddition of acyclic nitrones with phenyl isocyanate: Synthesis and ring-opening reactions of 1,2,4-oxadiazolidin-5-ones
Authors: Uludağ Üniversitesi/Fen-Edebiyat Fakültesi/Kimya Bölümü.
Coşkun, Necdet
Parlar, Aydın
7004177880
8937610400
Keywords: Chemistry
Substituent effect
Secamine induced fragmentation of 1,2,4-oxadiazolidin-5-ones
Acyclic nitrone
1,3-dipolar cycloaddition
1,2,4-oxadiazolidin-5-one
Regio
Aryl isocyanates
Diastereoselective addition
Imidazoline 3-oxides
Issue Date: 2006
Publisher: Taylor & Francis
Citation: Coşkun, N. ve Parlar, A. (2006). ''Cycloaddition of acyclic nitrones with phenyl isocyanate: Synthesis and ring-opening reactions of 1,2,4-oxadiazolidin-5-ones''. Synthetic Communications, 36(8), 997-1004.
Abstract: The cycloaddition of nitrones with unsubstituted or electron-donating substituents on the C-phenyl 1a,c,f with phenyl isocyanate proceeds smoothly for a short time with high yields to give the corresponding 1,2,4-oxadiazolidinone 2, and 1b,d,e with electron-withdrawing substituents gave the corresponding oxadiazolidinone in moderate yields after prolonged heating. Oxadiazolidinones 2a,c,f undergo diethylamine-induced fragmentation for a short time to give the corresponding Schiff bases, and oxadiazolidinones 2b,d,e remain unchanged in these conditions. Prolonged heating of 2d,e in the presence of diethylamine led to complex mixtures. In the case of 2b the corresponding amidine was the main product of the reaction.
URI: https://doi.org/10.1080/00397910500501466
https://www.tandfonline.com/doi/full/10.1080/00397910500501466
http://hdl.handle.net/11452/22995
ISSN: 0039-7911
Appears in Collections:Scopus
Web of Science

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