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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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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2017
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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. |
format | Online Article Text |
id | pubmed-6641687 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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