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Three-Component One-Pot Approach to Highly Efficient and Sustainable Synthesis of the Functionalized Quinolones via Linear/Branched Domino Protocols, Key Synthetic Methods for the Floxacin of Quinolone Drugs
[Image: see text] The development of a clear chemical process to produce diverse value-added chemicals from low-cost raw materials is a particularly attractive concept and represents a considerable challenge in sustainable organic synthesis. Herein, two highly efficient and clear methods for the syn...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2018
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645088/ https://www.ncbi.nlm.nih.gov/pubmed/31459232 http://dx.doi.org/10.1021/acsomega.8b01378 |
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author | Bai, Hairui Liu, Fujun Wang, Xiaojing Wang, Ping Huang, Chao |
author_facet | Bai, Hairui Liu, Fujun Wang, Xiaojing Wang, Ping Huang, Chao |
author_sort | Bai, Hairui |
collection | PubMed |
description | [Image: see text] The development of a clear chemical process to produce diverse value-added chemicals from low-cost raw materials is a particularly attractive concept and represents a considerable challenge in sustainable organic synthesis. Herein, two highly efficient and clear methods for the synthesis of quinolone derivatives based on a linear/branched domino protocol under sustainable conditions were established. The main advantages of these protocols are the simple experimental procedure, high bond-forming efficiency, inexpensive readily available starting materials, moderate to excellent yields with good functional group compatibility, and nonchromatographic purification, which render these methods particularly attractive for the sustainable preparation of biologically and medicinally interesting molecules. To demonstrate the practical utility of our protocol, existing pharmaceutical sarafloxacin was successfully synthesized. Furthermore, a postulated reaction pathway including condensation reaction/nucleophilic aromatic substitution/Friedel–Crafts reaction for these domino reactions is also discussed. |
format | Online Article Text |
id | pubmed-6645088 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-66450882019-08-27 Three-Component One-Pot Approach to Highly Efficient and Sustainable Synthesis of the Functionalized Quinolones via Linear/Branched Domino Protocols, Key Synthetic Methods for the Floxacin of Quinolone Drugs Bai, Hairui Liu, Fujun Wang, Xiaojing Wang, Ping Huang, Chao ACS Omega [Image: see text] The development of a clear chemical process to produce diverse value-added chemicals from low-cost raw materials is a particularly attractive concept and represents a considerable challenge in sustainable organic synthesis. Herein, two highly efficient and clear methods for the synthesis of quinolone derivatives based on a linear/branched domino protocol under sustainable conditions were established. The main advantages of these protocols are the simple experimental procedure, high bond-forming efficiency, inexpensive readily available starting materials, moderate to excellent yields with good functional group compatibility, and nonchromatographic purification, which render these methods particularly attractive for the sustainable preparation of biologically and medicinally interesting molecules. To demonstrate the practical utility of our protocol, existing pharmaceutical sarafloxacin was successfully synthesized. Furthermore, a postulated reaction pathway including condensation reaction/nucleophilic aromatic substitution/Friedel–Crafts reaction for these domino reactions is also discussed. American Chemical Society 2018-09-14 /pmc/articles/PMC6645088/ /pubmed/31459232 http://dx.doi.org/10.1021/acsomega.8b01378 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes. |
spellingShingle | Bai, Hairui Liu, Fujun Wang, Xiaojing Wang, Ping Huang, Chao Three-Component One-Pot Approach to Highly Efficient and Sustainable Synthesis of the Functionalized Quinolones via Linear/Branched Domino Protocols, Key Synthetic Methods for the Floxacin of Quinolone Drugs |
title | Three-Component One-Pot Approach to Highly Efficient
and Sustainable Synthesis of the Functionalized Quinolones via Linear/Branched
Domino Protocols, Key Synthetic Methods for the Floxacin of Quinolone
Drugs |
title_full | Three-Component One-Pot Approach to Highly Efficient
and Sustainable Synthesis of the Functionalized Quinolones via Linear/Branched
Domino Protocols, Key Synthetic Methods for the Floxacin of Quinolone
Drugs |
title_fullStr | Three-Component One-Pot Approach to Highly Efficient
and Sustainable Synthesis of the Functionalized Quinolones via Linear/Branched
Domino Protocols, Key Synthetic Methods for the Floxacin of Quinolone
Drugs |
title_full_unstemmed | Three-Component One-Pot Approach to Highly Efficient
and Sustainable Synthesis of the Functionalized Quinolones via Linear/Branched
Domino Protocols, Key Synthetic Methods for the Floxacin of Quinolone
Drugs |
title_short | Three-Component One-Pot Approach to Highly Efficient
and Sustainable Synthesis of the Functionalized Quinolones via Linear/Branched
Domino Protocols, Key Synthetic Methods for the Floxacin of Quinolone
Drugs |
title_sort | three-component one-pot approach to highly efficient
and sustainable synthesis of the functionalized quinolones via linear/branched
domino protocols, key synthetic methods for the floxacin of quinolone
drugs |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645088/ https://www.ncbi.nlm.nih.gov/pubmed/31459232 http://dx.doi.org/10.1021/acsomega.8b01378 |
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