3 + n] Cycloaddition Reactions: A Milestone Approach for Elaborating Pyridazine of Potential Interest in Medicinal Chemistry and Optoelectronics.

Dorina Amariucai-Mantu,Ionel I Mangalagiu,Violeta Mangalagiu

doi:10.3390/molecules26113359

Dorina Amariucai-Mantu, Ionel I Mangalagiu + Show 1 more

Open Access

https://doi.org/10.3390/molecules26113359

Copy DOI

Abstract

During the last few decades, pyridazine derivatives have emerged as privileged structures in heterocyclic chemistry, both because of their excellent chemistry and because of their potential applications in medicinal chemistry and optoelectronics. This review is focused on the recent advances in [3 + n] cycloaddition reactions in the pyridazine series as well as their medicinal chemistry and optoelectronic applications over the last ten years. The stereochemistry and regiochemistry of the cycloaddition reactions are discussed. Applications in optoelectronics (in particular, as fluorescent materials and sensors) and medicinal chemistry (in particular, antimicrobials and anticancer) are also reviewed.

Highlights

[3 + n] cycloaddition reactions represent one of the most important and efficient tools in the synthesis of heterocyclic rings, consisting of the addition of a multiple bond dipolarophile to a three-atom component system (TACS)
The [3 + 2] dipolar cycloaddition reactions were discovered by Rolf Huisgen in the early 1960s, more than 60 years ago [1,2]
The Huisgen [3 + 2] dipolar cycloaddition reactions represent an addition of a 1,3-dipole to a dipolarophile, leading to a five-membered heterocyclic ring [1,2,3,4,5,6,7], via a concerted mechanism, as presented in Scheme 1

Summary

Introduction

[3 + n] cycloaddition reactions represent one of the most important and efficient tools in the synthesis of heterocyclic rings, consisting of the addition of a multiple bond dipolarophile to a three-atom component system (TACS). On the other hand, [3 + 2] cycloaddition reactions represent an accessible and facile tool to obtain pyridazine derivatives of potential interest in medicinal chemistry (as antibacterials, antifungals, antituberculars, antivirals, anticancer agents, anti-inflammatories, antihypertensives, diuretics, etc.) [22,23] and in optoelectronics (as highly fluorescent materials, sensors and biosensors, lasers, etc.) [24].

Results

Conclusion