Three-Component Coupling Approach for the Synthesis of Diverse Heterocycles Utilizing Reactive Nitrilium Trapping
Year: 2014
Type: article
Abstract: 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.
Source: Organic Letters
DOI: 10.1021/ol500328t
Institutions: Memorial Sloan Kettering Cancer Center, New York University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Awards: G1287527835, G4719393010, Pharmacology of opioid actions in vivo, G5117853546, G546047228, Analgesics targeting truncated 6transmembrane exon 11 variants of MOR-1 (6TM-E11), Synthesis and pharmacology of novel opiates and their modulatory systems, PHARMACOLOGY OF OPIOID RECEPTOR SUBTYPES, Analgesics targeting truncated 6transmembrane exon 11 variants of MOR-1 (6TM-E11), G8027540620, Cancer Center Support Grant, Behavioral Pharmacology of Human Drug Use Disorders
OpenAlex ID: W2083492614