Sc(OTf)(3)-Mediated [4 + 2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction

[Image: see text] We disclose the first accomplishment of the azo-Povarov reaction involving Sc(OTf)(3)-catalyzed [4 + 2] annulations of N-carbonyl aryldiazenes with cyclopentadiene in chloroform, in which N-carbonyl aryldiazenes act as 4π-electron donors. Hence, this protocol offers a rapid access...

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Autores principales: Jiménez-Aberásturi, Xabier, Palacios, Francisco, de los Santos, Jesús M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9447289/
https://www.ncbi.nlm.nih.gov/pubmed/35972474
http://dx.doi.org/10.1021/acs.joc.2c01224
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author Jiménez-Aberásturi, Xabier
Palacios, Francisco
de los Santos, Jesús M.
author_facet Jiménez-Aberásturi, Xabier
Palacios, Francisco
de los Santos, Jesús M.
author_sort Jiménez-Aberásturi, Xabier
collection PubMed
description [Image: see text] We disclose the first accomplishment of the azo-Povarov reaction involving Sc(OTf)(3)-catalyzed [4 + 2] annulations of N-carbonyl aryldiazenes with cyclopentadiene in chloroform, in which N-carbonyl aryldiazenes act as 4π-electron donors. Hence, this protocol offers a rapid access to an array of cinnoline derivatives in moderate to good yields for substrates over a wide scope. The synthetic potential of the protocol was achieved by the gram-scale reaction and further derivatization of the obtained polycyclic product.
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spelling pubmed-94472892022-09-07 Sc(OTf)(3)-Mediated [4 + 2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction Jiménez-Aberásturi, Xabier Palacios, Francisco de los Santos, Jesús M. J Org Chem [Image: see text] We disclose the first accomplishment of the azo-Povarov reaction involving Sc(OTf)(3)-catalyzed [4 + 2] annulations of N-carbonyl aryldiazenes with cyclopentadiene in chloroform, in which N-carbonyl aryldiazenes act as 4π-electron donors. Hence, this protocol offers a rapid access to an array of cinnoline derivatives in moderate to good yields for substrates over a wide scope. The synthetic potential of the protocol was achieved by the gram-scale reaction and further derivatization of the obtained polycyclic product. American Chemical Society 2022-08-16 2022-09-02 /pmc/articles/PMC9447289/ /pubmed/35972474 http://dx.doi.org/10.1021/acs.joc.2c01224 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Jiménez-Aberásturi, Xabier
Palacios, Francisco
de los Santos, Jesús M.
Sc(OTf)(3)-Mediated [4 + 2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction
title Sc(OTf)(3)-Mediated [4 + 2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction
title_full Sc(OTf)(3)-Mediated [4 + 2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction
title_fullStr Sc(OTf)(3)-Mediated [4 + 2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction
title_full_unstemmed Sc(OTf)(3)-Mediated [4 + 2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction
title_short Sc(OTf)(3)-Mediated [4 + 2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction
title_sort sc(otf)(3)-mediated [4 + 2] annulations of n-carbonyl aryldiazenes with cyclopentadiene to construct cinnoline derivatives: azo-povarov reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9447289/
https://www.ncbi.nlm.nih.gov/pubmed/35972474
http://dx.doi.org/10.1021/acs.joc.2c01224
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