N,N′-Di-Boc-2H-Isoindole-2-carboxamidine—First Guanidine-Substituted Isoindole

Synthesis of N,N′-Di-Boc-2H-isoindole-2-carboxamidine, the first representative of isoindoles containing guanidine functionality, was carried out. The cycloaddition reactivity of this new Diels–Alder heterodiene was studied and the title compound was employed as a cycloaddition delivery reagent for...

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Detalles Bibliográficos
Autores principales: Štrbac, Petar, Briš, Anamarija, Margetić, Davor
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9781607/
https://www.ncbi.nlm.nih.gov/pubmed/36558087
http://dx.doi.org/10.3390/molecules27248954
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author Štrbac, Petar
Briš, Anamarija
Margetić, Davor
author_facet Štrbac, Petar
Briš, Anamarija
Margetić, Davor
author_sort Štrbac, Petar
collection PubMed
description Synthesis of N,N′-Di-Boc-2H-isoindole-2-carboxamidine, the first representative of isoindoles containing guanidine functionality, was carried out. The cycloaddition reactivity of this new Diels–Alder heterodiene was studied and the title compound was employed as a cycloaddition delivery reagent for guanidine functionality. Higher reactivity was found in comparison with the corresponding pyrrole derivative. Substitution with fluorine or guanidine functionality does not change the reactivities of isoindoles, and these findings are in good accord with computational results.
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spelling pubmed-97816072022-12-24 N,N′-Di-Boc-2H-Isoindole-2-carboxamidine—First Guanidine-Substituted Isoindole Štrbac, Petar Briš, Anamarija Margetić, Davor Molecules Article Synthesis of N,N′-Di-Boc-2H-isoindole-2-carboxamidine, the first representative of isoindoles containing guanidine functionality, was carried out. The cycloaddition reactivity of this new Diels–Alder heterodiene was studied and the title compound was employed as a cycloaddition delivery reagent for guanidine functionality. Higher reactivity was found in comparison with the corresponding pyrrole derivative. Substitution with fluorine or guanidine functionality does not change the reactivities of isoindoles, and these findings are in good accord with computational results. MDPI 2022-12-15 /pmc/articles/PMC9781607/ /pubmed/36558087 http://dx.doi.org/10.3390/molecules27248954 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
Štrbac, Petar
Briš, Anamarija
Margetić, Davor
N,N′-Di-Boc-2H-Isoindole-2-carboxamidine—First Guanidine-Substituted Isoindole
title N,N′-Di-Boc-2H-Isoindole-2-carboxamidine—First Guanidine-Substituted Isoindole
title_full N,N′-Di-Boc-2H-Isoindole-2-carboxamidine—First Guanidine-Substituted Isoindole
title_fullStr N,N′-Di-Boc-2H-Isoindole-2-carboxamidine—First Guanidine-Substituted Isoindole
title_full_unstemmed N,N′-Di-Boc-2H-Isoindole-2-carboxamidine—First Guanidine-Substituted Isoindole
title_short N,N′-Di-Boc-2H-Isoindole-2-carboxamidine—First Guanidine-Substituted Isoindole
title_sort n,n′-di-boc-2h-isoindole-2-carboxamidine—first guanidine-substituted isoindole
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9781607/
https://www.ncbi.nlm.nih.gov/pubmed/36558087
http://dx.doi.org/10.3390/molecules27248954
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