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

Autor:	William P. Henry, Hondamuni I. De Silva, Yingquan Song, Guozhong Ye, Charles U. Pittman
Rok vydání:	2011
Předmět:	chemistry.chemical_classification Aryl Organic Chemistry Iodide One-pot synthesis Ketene Biochemistry Medicinal chemistry Catalysis chemistry.chemical_compound chemistry Nucleophile Drug Discovery Lactam Triethylamine
Zdroj:	Tetrahedron Letters. 52:853-858
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2010.11.148
Popis:	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.
Databáze:	OpenAIRE
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