Synthesis of Novel Fluoropicolinate Herbicides by Cascade Cyclization of Fluoroalkyl Alkynylimines
| Autor: | Chris V. Galliford, Natalie C. Giampietro, James M. Renga, Peter L. Johnson, Gregory T. Whiteker |
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| Rok vydání: | 2015 |
| Předmět: |
chemistry.chemical_classification
Primary (chemistry) Molecular Structure Herbicides Aryl Organic Chemistry Acetal Aminopyridines Picolinic acid Biochemistry chemistry.chemical_compound chemistry Cyclization Organic chemistry Imines Physical and Theoretical Chemistry Picolinaldehyde Picolinic Acids Alkyl |
| Zdroj: | Organic Letters. 17:2905-2907 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.5b01176 |
| Popis: | The cascade cyclization of fluoroalkyl alkynylimines with primary amines has been modified to allow the synthesis of 4-amino-5-fluoropicolinates. Use of N-trityl and acetal protecting groups in the cyclization precursor led to 5-fluoropyridines that were easily deprotected to picolinaldehyde derivatives for further elaboration to structures of interest as potential herbicides. This method provided access to picolinic acids with alkyl or aryl substituents at the 6-position that were previously inaccessible via cross-coupling chemistry. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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