Bucha Mallaiah, Eppakayala Laxminarayana, Maringanti Thirumala Chary, Tharikoppula Giri, Kethireddy Shashikala
Mahatma Gandhi Institute of Technology, Gandipet, Hyderabad, 50075, Telangana, India.
Jawaharlal Nehru Technological University Hyderabad College of Engineering, Nachupally, Karimnagar, 505 501, Telangana, India.
Org Med Chem Lett. 2014 Dec;4(1):16. doi: 10.1186/s13588-014-0016-8. Epub 2014 Dec 21.
1,8-Naphthyridine derivatives have attracted considerable attention because the 1,8-naphthyridine skeleton is present in many compounds that have been isolated from natural substances, with various biological activities.
N,N-dimethoxy-N-methyl-1,8-naphthyridine-3-carboxamide (1) on reaction with Grignard reagent forms 2-methoxy-1,8-naphthyridine-3-carbaldehyde (2). Compound 2 on reaction with different aromatic aldehydes provided 1-(2-cyclopropyl-1,8-naphthyridin-3-yl)-3-arylprop-2-en-1-ones (3a-e) and these compounds on cyclisation with hydrazine hydrate 99% yielded 2-cyclopropyl-3-(5-aryl-1H-pyrazol-3-yl)-1,8-naphthyridines (4-a-e). Synthesis of the target compounds involved the formation of 4a-e. It was accomplished using Grignard reaction, condensation reaction, and cyclisation reactions. All the synthesized compounds were readily soluble in DMSO. Spectral data of the synthesized compounds were in full agreement with the proposed structures.
In conclusion, we have developed a simple and an efficient Synthesis of 2-cyclopropyl-3-(5-aryl-1H-pyrazol-3-yl)-1,8-naphthyridine.
1,8-萘啶衍生物备受关注，因为1,8-萘啶骨架存在于许多从天然物质中分离出的具有多种生物活性的化合物中。
N,N-二甲氧基-N-甲基-1,8-萘啶-3-甲酰胺（1）与格氏试剂反应生成2-甲氧基-1,8-萘啶-3-甲醛（2）。化合物2与不同的芳香醛反应得到1-(2-环丙基-1,8-萘啶-3-基)-3-芳基丙-2-烯-1-酮（3a - e），这些化合物与99%水合肼环化得到2-环丙基-3-(5-芳基-1H-吡唑-3-基)-1,8-萘啶（4 - a - e）。目标化合物的合成涉及4a - e的形成。它通过格氏反应、缩合反应和环化反应完成。所有合成的化合物都易溶于二甲基亚砜。合成化合物的光谱数据与所提出的结构完全一致。
总之，我们开发了一种简单有效的合成2-环丙基-3-(5-芳基-1H-吡唑-3-基)-1,8-萘啶的方法。
