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Acid-Catalyzed Air-Oxidative Fragmentation of the Carbon–Carbon Bond in 2-Aryl-1-tetralones
[Image: see text] Catalytic auto-oxidation with air is a highly desirable method for green synthesis. Described here is a method for acid-catalyzed one step air-oxidative fragmentation of 2-aryl-1-tetralones to alkyl-2-(3-oxo-3-aryl) benzoates in the presence of alcohol. This method was then demonst...
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2019
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648412/ https://www.ncbi.nlm.nih.gov/pubmed/31459896 http://dx.doi.org/10.1021/acsomega.9b00732 |
| _version_ | 1783437862720503808 |
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| author | Ghosh, Partha |
| author_facet | Ghosh, Partha |
| author_sort | Ghosh, Partha |
| collection | PubMed |
| description | [Image: see text] Catalytic auto-oxidation with air is a highly desirable method for green synthesis. Described here is a method for acid-catalyzed one step air-oxidative fragmentation of 2-aryl-1-tetralones to alkyl-2-(3-oxo-3-aryl) benzoates in the presence of alcohol. This method was then demonstrated using concise synthesis of a key intermediate of antiasthma drug Montelukast sodium. Moreover, the paradoxical nature of the reaction in which ester forms but only within a low concentration threshold of alcohol helps in understanding the mechanism of the reaction. |
| format | Online Article Text |
| id | pubmed-6648412 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2019 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-66484122019-08-27 Acid-Catalyzed Air-Oxidative Fragmentation of the Carbon–Carbon Bond in 2-Aryl-1-tetralones Ghosh, Partha ACS Omega [Image: see text] Catalytic auto-oxidation with air is a highly desirable method for green synthesis. Described here is a method for acid-catalyzed one step air-oxidative fragmentation of 2-aryl-1-tetralones to alkyl-2-(3-oxo-3-aryl) benzoates in the presence of alcohol. This method was then demonstrated using concise synthesis of a key intermediate of antiasthma drug Montelukast sodium. Moreover, the paradoxical nature of the reaction in which ester forms but only within a low concentration threshold of alcohol helps in understanding the mechanism of the reaction. American Chemical Society 2019-05-02 /pmc/articles/PMC6648412/ /pubmed/31459896 http://dx.doi.org/10.1021/acsomega.9b00732 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
| spellingShingle | Ghosh, Partha Acid-Catalyzed Air-Oxidative Fragmentation of the Carbon–Carbon Bond in 2-Aryl-1-tetralones |
| title | Acid-Catalyzed Air-Oxidative Fragmentation of the
Carbon–Carbon Bond in 2-Aryl-1-tetralones |
| title_full | Acid-Catalyzed Air-Oxidative Fragmentation of the
Carbon–Carbon Bond in 2-Aryl-1-tetralones |
| title_fullStr | Acid-Catalyzed Air-Oxidative Fragmentation of the
Carbon–Carbon Bond in 2-Aryl-1-tetralones |
| title_full_unstemmed | Acid-Catalyzed Air-Oxidative Fragmentation of the
Carbon–Carbon Bond in 2-Aryl-1-tetralones |
| title_short | Acid-Catalyzed Air-Oxidative Fragmentation of the
Carbon–Carbon Bond in 2-Aryl-1-tetralones |
| title_sort | acid-catalyzed air-oxidative fragmentation of the
carbon–carbon bond in 2-aryl-1-tetralones |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648412/ https://www.ncbi.nlm.nih.gov/pubmed/31459896 http://dx.doi.org/10.1021/acsomega.9b00732 |
| work_keys_str_mv | AT ghoshpartha acidcatalyzedairoxidativefragmentationofthecarboncarbonbondin2aryl1tetralones |