Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco/Euskal Herriko, Unibertsitatea (UPV/EHU), Paseo de la Universidad 7, 01006 Vitoria-Gasteiz, Spain.
Molecules. 2020 Jul 31;25(15):3508. doi: 10.3390/molecules25153508.
Heterocyclic nitrogen compounds, including fused 1,5-naphthyridines, have versatile applications in the fields of synthetic organic chemistry and play an important role in the field of medicinal chemistry, as many of them have a wide range of biological activities. In this review, a wide range of synthetic protocols for the construction of this scaffold are presented. For example, Friedländer, Skraup, Semmlere-Wolff, and hetero-Diels-Alder, among others, are well known classical synthetic protocols used for the construction of the main 1,5-naphthyridine scaffold. These syntheses are classified according to the nature of the cycle fused to the 1,5-naphthyridine ring: carbocycles, nitrogen heterocycles, oxygen heterocycles, and sulphur heterocycles. In addition, taking into account the aforementioned versatility of these heterocycles, their reactivity is presented as well as their use as a ligand for metal complexes formation. Finally, those fused 1,5-naphthyridines that present biological activity and optical applications, among others, are indicated.
杂环氮化合物,包括稠合的 1,5-萘啶,在合成有机化学领域有广泛的应用,并在药物化学领域发挥着重要作用,因为其中许多具有广泛的生物活性。在这篇综述中,展示了构建这个支架的多种合成方案。例如,Friedländer、Skraup、Semmlere-Wolff 和杂 Diels-Alder 等,都是用于构建主要的 1,5-萘啶骨架的著名经典合成方案。这些合成方法根据与 1,5-萘啶环稠合的环的性质进行分类:碳环、氮杂环、氧杂环和硫杂环。此外,考虑到这些杂环的上述多功能性,还介绍了它们的反应性以及它们作为金属配合物形成配体的用途。最后,指出了那些具有生物活性和光学应用等特性的稠合 1,5-萘啶。