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Stereoselective Synthesis of Polysubstituted Hydroquinolines in a One-pot, Pseudo-Eight-Component Strategy
Organic Preparations and Procedures International ( IF 1.2 ) Pub Date : 2019-11-02 , DOI: 10.1080/00304948.2019.1677992
Maryam Fatahpour 1 , Mojtaba Lashkari 2 , Nourallah Hazeri 1 , Fatemeh Noori Sadeh 1 , Malek Taher Maghsoodlou 1
Affiliation  

The synthesis of polyfunctionalized heterocyclic compounds has attracted great attention in the discovery and analysis of drugs. Procedures for the design and synthesis of novel complex polycyclic heterocycles with notable therapeutic and pharmacological properties have high priority in chemical synthesis. Spirocyclic scaffolds have raised broad interest due to their useful rearrangement reactions owing to the steric strain at the quaternary carbon atom. In the same vein, multi-component reactions (MCRs) have become pivotal tools for preparing libraries of diverse druggable heterocyclic compounds because of their high atom and step economy, simple execution, excellent yields, and ease of work-up. This in turn reduces the need for the isolation of intermediates and curbs waste generation. Quinolines represent a class of N-fused heterocycles which are ubiquitous in natural products and, in particular, in bioactive alkaloids. These compounds exhibit a broad range of biological and pharmacological properties, including antiviral, antifungal, anti-inflammatory, antibacterial, anticancer, antimalarial, and anti-HIV activities. Some antibiotic compounds based on the quinoline moiety are displayed in Figure 1. This family includes a number of significant antibiotics, including ciprofloxacin and levofloxacin. In recent years, the use of organocatalysis has blossomed in organic chemistry, and especially in the field of medicinal chemistry, as a fundamental tool in the synthesis of complex molecular motifs. Among organocatalysts, phthalic acid is easily prepared and is applied in the production of a range of chemicals. Considering the above facts and in continuation of our research on multi-component reactions with remarkable stereochemistry we now report a new and efficient one-pot, pseudo eight-component strategy for the rapid synthesis of

中文翻译:

多取代氢喹啉的立体选择性合成一锅、伪八组分策略

多功能杂环化合物的合成在药物的发现和分析中引起了极大的关注。具有显着治疗和药理特性的新型复杂多环杂环的设计和合成程序在化学合成中具有高度优先地位。由于季碳原子处的空间应变,螺环支架因其有用的重排反应而引起了广泛的兴趣。同样,多组分反应 (MCR) 已成为制备各种可成药杂环化合物库的关键工具,因为它们具有原子和步骤经济性高、执行简单、产率高且易于处理等优点。这反过来又减少了分离中间体的需要并抑制了废物的产生。喹啉代表一类在天然产物中普遍存在的 N 稠合杂环,特别是在生物活性生物碱中。这些化合物表现出广泛的生物学和药理学特性,包括抗病毒、抗真菌、抗炎、抗菌、抗癌、抗疟和抗 HIV 活性。图 1 显示了一些基于喹啉部分的抗生素化合物。该家族包括许多重要的抗生素,包括环丙沙星和左氧氟沙星。近年来,作为合成复杂分子基序的基本工具,有机催化在有机化学,特别是药物化学领域的应用蓬勃发展。在有机催化剂中,邻苯二甲酸易于制备,可用于生产一系列化学品。
更新日期:2019-11-02
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