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 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
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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. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2010.11.148 |