One pot synthesis of α,α-bis( N-arylamido) lactams via iodide-catalyzed rearrangement of β,β-bis( N-arylamido) cyclic ketene- N, O-acetals

Five and six-membered cyclic ketene- N, O-acetals, generated in situ from 2,3-dimethyl-2-oxazolinium iodide or 2,3-dimethyl-2-oxazinium iodide and triethylamine, reacted with aryl isocyanates in refluxing THF producing α,α-bis( N-arylamido) lactams via the iodide-catalyzed rearrangement of β,β-bis(...

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Veröffentlicht in:Tetrahedron letters 2011-02, Vol.52 (8), p.853-858
Hauptverfasser: Song, Yingquan, Henry, William P., De Silva, Hondamuni I., Ye, Guozhong, Pittman, Charles U.
Format: Artikel
Sprache:eng
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Zusammenfassung:Five and six-membered cyclic ketene- N, O-acetals, generated in situ from 2,3-dimethyl-2-oxazolinium iodide or 2,3-dimethyl-2-oxazinium iodide and triethylamine, reacted with aryl isocyanates in refluxing THF producing α,α-bis( N-arylamido) lactams via the iodide-catalyzed rearrangement of β,β-bis( N-arylamido) cyclic ketene- N, O-acetal intermediates. The cyclic ketene- N, O-acetal generated in situ from 2,3,4,4-tetramethyl-2-oxazolinium iodide reacted with isocyanates to give β,β-bis( N-arylamido) cyclic ketene- N, O-acetals, which do not readily rearrange. The two methyls at C-4 hindered the nucleophilic attack of iodide on C-5, which is required for rearrangement.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.11.148