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Organic & Biomolecular Chemistry

C4–C5 fused pyrazol-3-amines: when the degree of unsaturation and electronic characteristics of the fused ring controls regioselectivity in Ullmann and acylation reactions†

Check for updates Elisabeth Bou-Petit,a Arnau Plans,a Nieves Rodríguez-Picazo,a Antoni Torres-Coll,a Cristina Puigjaner, ORCID logo b Mercè Font-Bardia,b Jordi Teixidó, ORCID logo a Santiago Ramon y Cajal,c Roger Estrada-Tejedora and José I. Borrell ORCID logo *a Author affiliations

* Corresponding authors

a Grup de Química Farmacèutica, IQS School of Engineering, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona, Spain E-mail: [email protected]

b Unitat de Difracció de Raigs X, Centres Cientificotècnics, Universitat de Barcelona, Lluís Solè i Sabarís 1–3, 08028 Barcelona, Spain

c Departamento de Patología, Hospital Universitario Valle de Hebrón, Universidad Autónoma de Barcelona, Passeig Vall d'Hebron 119–129, 08035 Barcelona, Spain

Abstract

Pyrazol-3-amine is a scaffold present in a large number of compounds with a wide range of biological activities and, in many cases, the heterocycle is C4–C5 fused to a second ring. Among the different reactions used for the decoration of the pyrazole ring, Ullmann and acylation have been widely applied. However, there is some confusion in the literature regarding the regioselectivity of such reactions (substitution at N1 or N2 of the pyrazole ring) and no predictive rule has been so far established. As a part of our work on 3-amino-pyrazolo[3,4-b]pyridones 13, we have studied the regioselectivity of such reactions in different C4–C5 fused pyrazol-3-amines. As a rule of thumb, the Ullmann and acylation reactions take place, predominantly, at the NH and non-protonated nitrogen atom of the pyrazole ring respectively, of the most stable initial tautomer (1H- or 2H-pyrazole), which can be easily predicted by using DFT calculations.

Graphical abstract: C4–C5 fused pyrazol-3-amines: when the degree of unsaturation and electronic characteristics of the fused ring controls regioselectivity in Ullmann and acylation reactions
  • This article is part of the themed collection: Synthetic methodology in OBC
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Supplementary files

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Article information

DOI https://doi.org/10.1039/D0OB00796J Article type Paper Submitted 17 Apr 2020 Accepted 17 Jun 2020 First published 17 Jun 2020

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Org. Biomol. Chem., 2020,18, 5145-5156 BibTex EndNote MEDLINE ProCite ReferenceManager RefWorks RIS

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C4–C5 fused pyrazol-3-amines: when the degree of unsaturation and electronic characteristics of the fused ring controls regioselectivity in Ullmann and acylation reactions

E. Bou-Petit, A. Plans, N. Rodríguez-Picazo, A. Torres-Coll, C. Puigjaner, M. Font-Bardia, J. Teixidó, S. Ramon y Cajal, R. Estrada-Tejedor and J. I. Borrell, Org. Biomol. Chem., 2020, 18, 5145 DOI: 10.1039/D0OB00796J

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Elisabeth Bou-Petit Arnau Plans Nieves Rodríguez-Picazo Antoni Torres-Coll Cristina Puigjaner Mercè Font-Bardia Jordi Teixidó Santiago Ramon y Cajal Roger Estrada-Tejedor José I. Borrell

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