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Chromatography-Free Entry to Substituted Salicylonitriles: Mitsunobu-Triggered Domino Reactions of Salicylaldoximes.
- Source :
-
Journal of Organic Chemistry . 1/16/2015, Vol. 80 Issue 2, p1229-1234. 6p. - Publication Year :
- 2015
-
Abstract
- A mild and efficient one-pot procedure is described to transform salicylaldoximes into salicylonitriles using Mitsunobu chemistry. The reactions proceed through the corresponding 1,2-benzisoxazoles that undergo the Kemp elimination in situ to generate the target salicylonitriles in excellent yields. The chemistry exhibits a broad scope, and the salicylonitriles can be readily isolated by a simple acid-base workup. In addition to functioning as useful synthetic precursors, salicylonitriles may serve as more cell penetrable bioisosteres of carboxylic acids. [ABSTRACT FROM AUTHOR]
- Subjects :
- *NITRILES
*ORGANONITROGEN compounds
*BARTON reactions
*ALDOXIMES
*ALDEHYDES
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 80
- Issue :
- 2
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 101085420
- Full Text :
- https://doi.org/10.1021/jo502396u