127894-05-7Relevant articles and documents
Three-component coupling approach for the synthesis of diverse heterocycles utilizing reactive nitrilium trapping
Varadi, Andras,Palmer, Travis C.,Notis, Paula R.,Redel-Traub, Gabriel N.,Afonin, Daniel,Subrath, Joan J.,Pasternak, Gavril W.,Hu, Chunhua,Sharma, Indrajeet,Majumdar, Susruta
supporting information, p. 1668 - 1671 (2014/04/17)
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.
