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融合的 1,5-萘啶:合成工具和应用。

Fused 1,5-Naphthyridines: Synthetic Tools and Applications.

机构信息

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.

出版信息

Molecules. 2020 Jul 31;25(15):3508. doi: 10.3390/molecules25153508.

DOI:10.3390/molecules25153508
PMID:32752070
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7436086/
Abstract

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.

摘要

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。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d4b/7436086/25f24005d362/molecules-25-03508-sch019.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d4b/7436086/25f24005d362/molecules-25-03508-sch019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d4b/7436086/d4b421585b4f/molecules-25-03508-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d4b/7436086/04485107e341/molecules-25-03508-g002.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d4b/7436086/1503dc1150f8/molecules-25-03508-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d4b/7436086/82cfb8f84992/molecules-25-03508-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d4b/7436086/b5f3115d7f7c/molecules-25-03508-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d4b/7436086/610970919a28/molecules-25-03508-sch014.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d4b/7436086/6fafa03fd8f9/molecules-25-03508-sch016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d4b/7436086/8c9e9a9ed33b/molecules-25-03508-sch017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d4b/7436086/b1627bf311c5/molecules-25-03508-sch018.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d4b/7436086/25f24005d362/molecules-25-03508-sch019.jpg

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