Three-component coupling approach for the synthesis of diverse heterocycles utilizing reactive nitrilium trapping Journal Article
| Authors: | Varadi, A.; Palmer, T. C.; Notis, P. R.; Redel-Traub, G. N.; Afonin, D.; Subrath, J. J.; Pasternak, G. W.; Hu, C.; Sharma, I.; Majumdar, S. |
| Article Title: | Three-component coupling approach for the synthesis of diverse heterocycles utilizing reactive nitrilium trapping |
| 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. © 2014 American Chemical Society. |
| Journal Title: | Organic Letters |
| Volume: | 16 |
| Issue: | 6 |
| ISSN: | 1523-7060 |
| Publisher: | American Chemical Society |
| Date Published: | 2014-03-01 |
| Start Page: | 1668 |
| End Page: | 1671 |
| Language: | English |
| DOI: | 10.1021/ol500328t |
| PROVIDER: | scopus |
| PMCID: | PMC3969103 |
| PUBMED: | 24580074 |
| DOI/URL: | |
| Notes: | Export Date: 1 May 2014 -- CODEN: ORLEF -- Source: Scopus |
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