One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P(®) activation of 3-arylpropiolic acids

In situ activation of 3-arylpropiolic acids with T3P(®) (n-propylphosphonic acid anhydride) initiates a domino reaction furnishing 4-arylnaphtho[2,3-c]furan-1,3-diones in excellent yields. Upon employing these anhydrides as reactive intermediates blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-...

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Autores principales: Denißen, Melanie, Kraus, Alexander, Reiss, Guido J, Müller, Thomas J J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5687056/
https://www.ncbi.nlm.nih.gov/pubmed/29181114
http://dx.doi.org/10.3762/bjoc.13.231
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author Denißen, Melanie
Kraus, Alexander
Reiss, Guido J
Müller, Thomas J J
author_facet Denißen, Melanie
Kraus, Alexander
Reiss, Guido J
Müller, Thomas J J
author_sort Denißen, Melanie
collection PubMed
description In situ activation of 3-arylpropiolic acids with T3P(®) (n-propylphosphonic acid anhydride) initiates a domino reaction furnishing 4-arylnaphtho[2,3-c]furan-1,3-diones in excellent yields. Upon employing these anhydrides as reactive intermediates blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones are formed by consecutive pseudo three-component syntheses in a one-pot fashion. The Stokes shifts correlate excellently with the Hammett–Taft σ(R) parameter indicating an extended degree of resonance stabilization in the vibrationally relaxed excited singlet state.
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spelling pubmed-56870562017-11-27 One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P(®) activation of 3-arylpropiolic acids Denißen, Melanie Kraus, Alexander Reiss, Guido J Müller, Thomas J J Beilstein J Org Chem Full Research Paper In situ activation of 3-arylpropiolic acids with T3P(®) (n-propylphosphonic acid anhydride) initiates a domino reaction furnishing 4-arylnaphtho[2,3-c]furan-1,3-diones in excellent yields. Upon employing these anhydrides as reactive intermediates blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones are formed by consecutive pseudo three-component syntheses in a one-pot fashion. The Stokes shifts correlate excellently with the Hammett–Taft σ(R) parameter indicating an extended degree of resonance stabilization in the vibrationally relaxed excited singlet state. Beilstein-Institut 2017-11-03 /pmc/articles/PMC5687056/ /pubmed/29181114 http://dx.doi.org/10.3762/bjoc.13.231 Text en Copyright © 2017, Denißen et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Denißen, Melanie
Kraus, Alexander
Reiss, Guido J
Müller, Thomas J J
One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P(®) activation of 3-arylpropiolic acids
title One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P(®) activation of 3-arylpropiolic acids
title_full One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P(®) activation of 3-arylpropiolic acids
title_fullStr One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P(®) activation of 3-arylpropiolic acids
title_full_unstemmed One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P(®) activation of 3-arylpropiolic acids
title_short One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P(®) activation of 3-arylpropiolic acids
title_sort one-pot syntheses of blue-luminescent 4-aryl-1h-benzo[f]isoindole-1,3(2h)-diones by t3p(®) activation of 3-arylpropiolic acids
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5687056/
https://www.ncbi.nlm.nih.gov/pubmed/29181114
http://dx.doi.org/10.3762/bjoc.13.231
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