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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...

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Autores principales: Bai, Hairui, Liu, Fujun, Wang, Xiaojing, Wang, Ping, Huang, Chao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
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.
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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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