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The Use of Aryl-Substituted Homophthalic Anhydrides in the Castagnoli–Cushman Reaction Provides Access to Novel Tetrahydroisoquinolone Carboxylic Acid Bearing an All-Carbon Quaternary Stereogenic Center

Novel aryl-substituted homophthalic acids were cyclodehydrated to the respective homophthalic anhydrides for use in the Castagnoli–Cushman reaction. With a range of imines, this reaction proceeded smoothly and delivered hitherto undescribed 4-aryl-substituted tetrahydroisoquinolonic acids with remar...

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Autores principales: Moshnenko, Nazar, Kazantsev, Alexander, Bakulina, Olga, Dar’in, Dmitry, Krasavin, Mikhail
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9738897/
https://www.ncbi.nlm.nih.gov/pubmed/36500582
http://dx.doi.org/10.3390/molecules27238462
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author Moshnenko, Nazar
Kazantsev, Alexander
Bakulina, Olga
Dar’in, Dmitry
Krasavin, Mikhail
author_facet Moshnenko, Nazar
Kazantsev, Alexander
Bakulina, Olga
Dar’in, Dmitry
Krasavin, Mikhail
author_sort Moshnenko, Nazar
collection PubMed
description Novel aryl-substituted homophthalic acids were cyclodehydrated to the respective homophthalic anhydrides for use in the Castagnoli–Cushman reaction. With a range of imines, this reaction proceeded smoothly and delivered hitherto undescribed 4-aryl-substituted tetrahydroisoquinolonic acids with remarkable diastereoselectivity, good yields and no need for chromatographic purification. These findings significantly extend the range of cyclic anhydrides employable in the Castagnoli–Cushman reaction and signify access to a novel substitution pattern around the medicinally relevant tetrahydroisoquinolonic acid scaffold.
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spelling pubmed-97388972022-12-11 The Use of Aryl-Substituted Homophthalic Anhydrides in the Castagnoli–Cushman Reaction Provides Access to Novel Tetrahydroisoquinolone Carboxylic Acid Bearing an All-Carbon Quaternary Stereogenic Center Moshnenko, Nazar Kazantsev, Alexander Bakulina, Olga Dar’in, Dmitry Krasavin, Mikhail Molecules Article Novel aryl-substituted homophthalic acids were cyclodehydrated to the respective homophthalic anhydrides for use in the Castagnoli–Cushman reaction. With a range of imines, this reaction proceeded smoothly and delivered hitherto undescribed 4-aryl-substituted tetrahydroisoquinolonic acids with remarkable diastereoselectivity, good yields and no need for chromatographic purification. These findings significantly extend the range of cyclic anhydrides employable in the Castagnoli–Cushman reaction and signify access to a novel substitution pattern around the medicinally relevant tetrahydroisoquinolonic acid scaffold. MDPI 2022-12-02 /pmc/articles/PMC9738897/ /pubmed/36500582 http://dx.doi.org/10.3390/molecules27238462 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Moshnenko, Nazar
Kazantsev, Alexander
Bakulina, Olga
Dar’in, Dmitry
Krasavin, Mikhail
The Use of Aryl-Substituted Homophthalic Anhydrides in the Castagnoli–Cushman Reaction Provides Access to Novel Tetrahydroisoquinolone Carboxylic Acid Bearing an All-Carbon Quaternary Stereogenic Center
title The Use of Aryl-Substituted Homophthalic Anhydrides in the Castagnoli–Cushman Reaction Provides Access to Novel Tetrahydroisoquinolone Carboxylic Acid Bearing an All-Carbon Quaternary Stereogenic Center
title_full The Use of Aryl-Substituted Homophthalic Anhydrides in the Castagnoli–Cushman Reaction Provides Access to Novel Tetrahydroisoquinolone Carboxylic Acid Bearing an All-Carbon Quaternary Stereogenic Center
title_fullStr The Use of Aryl-Substituted Homophthalic Anhydrides in the Castagnoli–Cushman Reaction Provides Access to Novel Tetrahydroisoquinolone Carboxylic Acid Bearing an All-Carbon Quaternary Stereogenic Center
title_full_unstemmed The Use of Aryl-Substituted Homophthalic Anhydrides in the Castagnoli–Cushman Reaction Provides Access to Novel Tetrahydroisoquinolone Carboxylic Acid Bearing an All-Carbon Quaternary Stereogenic Center
title_short The Use of Aryl-Substituted Homophthalic Anhydrides in the Castagnoli–Cushman Reaction Provides Access to Novel Tetrahydroisoquinolone Carboxylic Acid Bearing an All-Carbon Quaternary Stereogenic Center
title_sort use of aryl-substituted homophthalic anhydrides in the castagnoli–cushman reaction provides access to novel tetrahydroisoquinolone carboxylic acid bearing an all-carbon quaternary stereogenic center
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9738897/
https://www.ncbi.nlm.nih.gov/pubmed/36500582
http://dx.doi.org/10.3390/molecules27238462
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