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Amine-Triggered Highly Facile Oxidative Benzannulation Reaction for the Synthesis of Anthranilates under Solvent-Free Calcium(II) Catalysis

[Image: see text] An amine-triggered facile synthetic approach of anthranilates has been described through benzannulation of readily available chemicals under one-pot solvent-free conditions using Ca(OTf)(2) as the sustainable catalyst. In this regioselective approach, we described a reasonably long...

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Autores principales: Yaragorla, Srinivasarao, Dada, Ravikrishna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641687/
https://www.ncbi.nlm.nih.gov/pubmed/31457765
http://dx.doi.org/10.1021/acsomega.7b00753
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author Yaragorla, Srinivasarao
Dada, Ravikrishna
author_facet Yaragorla, Srinivasarao
Dada, Ravikrishna
author_sort Yaragorla, Srinivasarao
collection PubMed
description [Image: see text] An amine-triggered facile synthetic approach of anthranilates has been described through benzannulation of readily available chemicals under one-pot solvent-free conditions using Ca(OTf)(2) as the sustainable catalyst. In this regioselective approach, we described a reasonably longer cascade, which proceeds through β-enamino ester formation/Michael addition/intramolecular aldol reaction/elimination/aromatization/oxidative debenzylation/lactonization with a broad substrate scope and high yields. The isolation of intermediates authenticated the mechanism, and the synthetic utility of the products was also demonstrated.
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spelling pubmed-66416872019-08-27 Amine-Triggered Highly Facile Oxidative Benzannulation Reaction for the Synthesis of Anthranilates under Solvent-Free Calcium(II) Catalysis Yaragorla, Srinivasarao Dada, Ravikrishna ACS Omega [Image: see text] An amine-triggered facile synthetic approach of anthranilates has been described through benzannulation of readily available chemicals under one-pot solvent-free conditions using Ca(OTf)(2) as the sustainable catalyst. In this regioselective approach, we described a reasonably longer cascade, which proceeds through β-enamino ester formation/Michael addition/intramolecular aldol reaction/elimination/aromatization/oxidative debenzylation/lactonization with a broad substrate scope and high yields. The isolation of intermediates authenticated the mechanism, and the synthetic utility of the products was also demonstrated. American Chemical Society 2017-08-23 /pmc/articles/PMC6641687/ /pubmed/31457765 http://dx.doi.org/10.1021/acsomega.7b00753 Text en Copyright © 2017 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 Yaragorla, Srinivasarao
Dada, Ravikrishna
Amine-Triggered Highly Facile Oxidative Benzannulation Reaction for the Synthesis of Anthranilates under Solvent-Free Calcium(II) Catalysis
title Amine-Triggered Highly Facile Oxidative Benzannulation Reaction for the Synthesis of Anthranilates under Solvent-Free Calcium(II) Catalysis
title_full Amine-Triggered Highly Facile Oxidative Benzannulation Reaction for the Synthesis of Anthranilates under Solvent-Free Calcium(II) Catalysis
title_fullStr Amine-Triggered Highly Facile Oxidative Benzannulation Reaction for the Synthesis of Anthranilates under Solvent-Free Calcium(II) Catalysis
title_full_unstemmed Amine-Triggered Highly Facile Oxidative Benzannulation Reaction for the Synthesis of Anthranilates under Solvent-Free Calcium(II) Catalysis
title_short Amine-Triggered Highly Facile Oxidative Benzannulation Reaction for the Synthesis of Anthranilates under Solvent-Free Calcium(II) Catalysis
title_sort amine-triggered highly facile oxidative benzannulation reaction for the synthesis of anthranilates under solvent-free calcium(ii) catalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641687/
https://www.ncbi.nlm.nih.gov/pubmed/31457765
http://dx.doi.org/10.1021/acsomega.7b00753
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