Three-Component Coupling Approach for the Synthesis of Diverse Heterocycles Utilizing Reactive Nitrilium Trapping

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• 作者：Andr谩s V谩radi ; Travis C. Palmer ; Paula R. Notis ; Gabriel N. Redel-Traub ; Daniel Afonin ; Joan J. Subrath ; Gavril W. Pasternak ; Chunhua Hu ; Indrajeet Sharma ; Susruta Majumdar
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：March 21, 2014
• 年：2014
• 卷：16
• 期：6
• 页码：1668-1671
• 全文大小：299K
• 年卷期：v.16,no.6(March 21, 2014)
• ISSN：1523-7052

文摘

The formation of an unexpected heterocyclic scaffold, a benzoxazole, in a three-component reaction between a ketone, isocyanide, and 2-aminophenol was encountered. This reaction involved a benzo[b][1,4]oxazine intermediate resulting from intramolecular attack of the aminophenol hydroxyl group on the nitrilium ion. Unlike previous literature examples, the trapped nitrilium benzo[b][1,4]oxazine could readily be subjected to ring opening with bis-nucleophiles. The reaction scope includes simple linear as well as complex cyclic ketones and substituted 2-aminophenols. A representative benzoxazole product could be further diversified to yield drug-like compounds.