Chemoselective synthesis of isolated and fused fluorenones and their photophysical and antiviral properties,Organic & Biomolecular Chemistry

当前位置： X-MOL 学术 › Org. Biomol. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Chemoselective synthesis of isolated and fused fluorenones and their photophysical and antiviral properties
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-09-19 , DOI: 10.1039/c8ob01733f
Ismail Althagafi _{1,

2,

3,

4,

5} , Ranjay Shaw _{1,

6,

7,

8} , Cheng-Run Tang _{9,

10,

11,

12,

13} , Rahul Panwar _{1,

6,

7,

8} , Shally Shally _{1,

6,

7,

8} , Chanda Sinha _{1,

6,

7,

8} , Amit Kumar _{1,

14,

15,

16} , Yong-Tang Zheng _{9,

10,

11,

12,

13} , Ramendra Pratap _{1,

6,

7,

8}

Affiliation

Highly functionalized fluorenones were synthesized by an intramolecular cyclization of 2′′-halo-[1,1′:3′,1′′-terphenyl]-4′-carbonitriles in the presence of n-butyllithium or lithium aluminium hydride. The precursor was synthesized by ring transformation of 2-oxo-6-aryl/heteroaryl-4-(sec.amino)-2H-pyran-3-carbonitriles or 2-oxobenzo[h]chromenes with o-bromo/chloro/fluoro-acetophenone under basic conditions in moderate yield. We performed the control experiment to understand the proposed mechanism and found that the presence of a secondary amine in the starting material directs the reactivity. The photophysical properties of 3-methoxy-7-(piperidin-1-yl)-5H-indeno[2,1-b]phenanthren-8(6H)-one was explored and solvent dependent emission was observed. These compounds were also tested against HIV-1 and low to moderate activity was observed.

中文翻译：

分离和融合的芴酮的化学选择性合成及其光物理和抗病毒特性

在正丁基锂或氢化铝锂的存在下，通过分子内环化2''-卤代-[1,1'：3'，1''-三联苯] -4'-腈来合成高度官能化的芴酮。通过将2-氧代-6-芳基/杂芳基-4-（仲氨基）-2 H-吡喃-3-甲腈或2-氧代苯并[ h ]色烯与邻-溴/氯/氟环转移来合成前体-苯乙酮在碱性条件下产率中等。我们进行了对照实验，以了解所提出的机理，并发现起始原料中仲胺的存在指导反应性。3-甲氧基-7-（哌啶-1-基）-5 H-茚三酮[2,1- b]的光物理性质探索了] phenanthren-8（6 H）-one并观察到溶剂依赖性发射。还测试了这些化合物的抗HIV-1活性，并观察到低至中等的活性。

更新日期：2018-10-18

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11