Revisiting the Structure and Chemistry of 3(5)-Substituted Pyrazoles

Secrieru, Alina, O'Neill, Paul Michael and Cristiano, Maria Lurdes Santos (2020) Revisiting the Structure and Chemistry of 3(5)-Substituted Pyrazoles. MOLECULES, 25 (1). E42-.

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Official URL: http://dx.doi.org/10.3390/molecules25010042

Abstract

Pyrazoles are known as versatile scaffolds in organic synthesis and medicinal chemistry, often used as starting materials for the preparation of more complex heterocyclic systems with relevance in the pharmaceutical field. Pyrazoles are also interesting compounds from a structural viewpoint, mainly because they exhibit tautomerism. This phenomenon may influence their reactivity, with possible impact on the synthetic strategies where pyrazoles take part, as well as on the biological activities of targets bearing a pyrazole moiety, since a change in structure translates into changes in properties. Investigations of the structure of pyrazoles that unravel the tautomeric and conformational preferences are therefore of upmost relevance. 3(5)-Aminopyrazoles are largely explored as precursors in the synthesis of condensed heterocyclic systems, namely pyrazolo[1,5-a]pyrimidines. However, the information available in the literature concerning the structure and chemistry of 3(5)-aminopyrazoles is scarce and disperse. We provide a revision of data on the present subject, based on investigations using theoretical and experimental methods, together with the applications of the compounds in synthesis. It is expected that the combined information will contribute to a deeper understanding of structure/reactivity relationships in this class of heterocycles, with a positive impact in the design of synthetic methods, where they take part.

Item Type:	Article
Uncontrolled Keywords:	pyrazoles, tautomerism, prototropy, annular tautomerism, reactivity, 3(5)-aminopyrazoles, heterocyclic synthesis, pyrazolo[1,5-a]pyrimidines
Depositing User:	Symplectic Admin
Date Deposited:	21 Oct 2020 10:02
Last Modified:	18 Jan 2023 23:26
DOI:	10.3390/molecules25010042
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3104777