Synthesis of Asthma Drug Zafirlukast (Accolate) Using Intramolecular Oxidative Coupling via sp(3) C–H Bond Activation

[Image: see text] The FDA-approved drug for the treatment of asthma, zafirlukast, is synthesized engaging multiple catalytic reactions including a new method for the construction of 3-aroylindoles via oxidative cyclization. The highlights include transition-metal and peroxide free C–H bond activatio...

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Autores principales: Paladugu, Srinu, Mainkar, Prathama S., Chandrasekhar, Srivari
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641481/
https://www.ncbi.nlm.nih.gov/pubmed/31458657
http://dx.doi.org/10.1021/acsomega.8b00476
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author Paladugu, Srinu
Mainkar, Prathama S.
Chandrasekhar, Srivari
author_facet Paladugu, Srinu
Mainkar, Prathama S.
Chandrasekhar, Srivari
author_sort Paladugu, Srinu
collection PubMed
description [Image: see text] The FDA-approved drug for the treatment of asthma, zafirlukast, is synthesized engaging multiple catalytic reactions including a new method for the construction of 3-aroylindoles via oxidative cyclization. The highlights include transition-metal and peroxide free C–H bond activation using the stoichiometric amount of sodium persulfate as an oxidizing agent in the construction of 3-aroylindole, avoiding transition metal, with over 28% overall yield. The complete process has a turnaround time of 28 h to get the target molecule starting from substituted aniline, with practically no protecting groups.
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spelling pubmed-66414812019-08-27 Synthesis of Asthma Drug Zafirlukast (Accolate) Using Intramolecular Oxidative Coupling via sp(3) C–H Bond Activation Paladugu, Srinu Mainkar, Prathama S. Chandrasekhar, Srivari ACS Omega [Image: see text] The FDA-approved drug for the treatment of asthma, zafirlukast, is synthesized engaging multiple catalytic reactions including a new method for the construction of 3-aroylindoles via oxidative cyclization. The highlights include transition-metal and peroxide free C–H bond activation using the stoichiometric amount of sodium persulfate as an oxidizing agent in the construction of 3-aroylindole, avoiding transition metal, with over 28% overall yield. The complete process has a turnaround time of 28 h to get the target molecule starting from substituted aniline, with practically no protecting groups. American Chemical Society 2018-04-16 /pmc/articles/PMC6641481/ /pubmed/31458657 http://dx.doi.org/10.1021/acsomega.8b00476 Text en Copyright © 2018 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 Paladugu, Srinu
Mainkar, Prathama S.
Chandrasekhar, Srivari
Synthesis of Asthma Drug Zafirlukast (Accolate) Using Intramolecular Oxidative Coupling via sp(3) C–H Bond Activation
title Synthesis of Asthma Drug Zafirlukast (Accolate) Using Intramolecular Oxidative Coupling via sp(3) C–H Bond Activation
title_full Synthesis of Asthma Drug Zafirlukast (Accolate) Using Intramolecular Oxidative Coupling via sp(3) C–H Bond Activation
title_fullStr Synthesis of Asthma Drug Zafirlukast (Accolate) Using Intramolecular Oxidative Coupling via sp(3) C–H Bond Activation
title_full_unstemmed Synthesis of Asthma Drug Zafirlukast (Accolate) Using Intramolecular Oxidative Coupling via sp(3) C–H Bond Activation
title_short Synthesis of Asthma Drug Zafirlukast (Accolate) Using Intramolecular Oxidative Coupling via sp(3) C–H Bond Activation
title_sort synthesis of asthma drug zafirlukast (accolate) using intramolecular oxidative coupling via sp(3) c–h bond activation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641481/
https://www.ncbi.nlm.nih.gov/pubmed/31458657
http://dx.doi.org/10.1021/acsomega.8b00476
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