Metal-Free Synthesis of 1,2,4-Triazines via a Coupled Domino Process in One-Pot | |
Department | ERC国家工程研究中心 |
Wang, Jing1; Tang, Dong2; Li, Zhuo-Mei3; Wu, Ping1; Meng X(孟旭)4; Liu, Ya-Feng1; Lu, Guo-Qiang1; Chen BH(陈保华)1; Chen BH(陈保华) | |
The second department | osso国家重点实验室 |
2017 | |
Source Publication | Current Organic Chemistry |
ISSN | 1385-2728 |
Volume | 21Issue:2Pages:183-188 |
Abstract | Background: 1,2,4-Triazine is a prominent structural core system present in numerous natural and synthetic biologically active compounds. The existing synthetic methodologies have mostly focused on 3,6- disubstituted-1,2,4-triazines and 3,5,6-trisubstituted-1,2,4-triazines. However, until now only a few methods have been developed for making 3,5-disubstituted-1,2,4-triazines. Objective: The primary objective of the study was to find an efficient and simple way to construct 3,5- disubstituted-1,2,4-triazines. Method: The arylethene (0.24 mmol), I2 (0.22 mmol), IBX(0.24mmol.) and DMSO (2 mL) were added to a round-bottomed flask equipped with a magnetic stirring bar. The reaction mixture was agitated at 110°C under air for 3h, then amidrazone (0.2 mmol) was added to the mixture and the reaction continued at 110°C for another 1.5h. Afterwards, water (20mL) was added and the reaction mixture was extracted with ethyl acetate (3 × 50mL). The organic phases was combined and concentrated under reduced pressure to distill ethyl acetate. The residue was further purified by column chromatography on a silica gel column with petroleum / ethyl acetate (5:1) as eluent to obtain the desired products. Results: We developed an operationally simple way of regioselectively synthesizing 3,5-disubstituted-1,2,4- triazines by a coupled domino strategy with terminal aryl alkenes and amidrazones in one-pot. The overall process involves three different reactions: iodination, Kornblum oxidation and condensation. Conclusion: The strategies exhibit high performance with moderate to high yields, using simple and readily available terminal aryl alkenes and amidrazones, representing a powerful tool for the formation of potentially biologically active derivatives. |
Keyword | Domino Strategy 1 Aryl Alkenes 2 Amidrazones 4-triazines Kornblum Oxidation Metal-free |
Subject Area | 物理化学与绿色催化 |
DOI | 10.2174/1385272820666160919113406 |
Funding Organization | the National Science Foundation of P. R. China (Nos. J11003307;21372102) |
Indexed By | SCI |
If | 1.924 |
Language | 英语 |
Funding Project | 催化新工艺研究组 |
compositor | 第四作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/21215 |
Collection | 精细石油化工中间体国家工程研究中心(ERC) 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Chen BH(陈保华) |
Affiliation | 1.State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Gansu Lanzhou 730000, P. R. China, and Key Laboratory Nonferrous Metal Chemistry & Resources Utilization of Gansu Province, Lanzhou 730000, P. R. China 2.Deptartment of Chemistry, Lishui University, Lishui 323000, P. R. China 3.Lanzhou University, High School, Gansu Lanzhou 730000, P. R. China 4.State Key Laboratory of Oxo Synthesis & Selective Oxidation, Lanzhou Institute Chemical Physics, Chinese Academy Sciences, Lanzhou 730000, P. R. China |
Recommended Citation GB/T 7714 | Wang, Jing,Tang, Dong,Li, Zhuo-Mei,et al. Metal-Free Synthesis of 1,2,4-Triazines via a Coupled Domino Process in One-Pot[J]. Current Organic Chemistry,2017,21(2):183-188. |
APA | Wang, Jing.,Tang, Dong.,Li, Zhuo-Mei.,Wu, Ping.,Meng X.,...&陈保华.(2017).Metal-Free Synthesis of 1,2,4-Triazines via a Coupled Domino Process in One-Pot.Current Organic Chemistry,21(2),183-188. |
MLA | Wang, Jing,et al."Metal-Free Synthesis of 1,2,4-Triazines via a Coupled Domino Process in One-Pot".Current Organic Chemistry 21.2(2017):183-188. |
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LZ01029656.pdf(943KB) | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Application Full Text |
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