2,6-二甲氧基吡啶溴代反应条件的研究
PDF下载 (422)王君平 1,樊一旭 1,梁明明 2,俞方杰 1,江 峰 1,梁洪泽 1*.2,6-二甲氧基吡啶溴代反应条件的研究[J].宁波大学学报(理工版),2015,28(04):90-92.DOI:
WANG Jun-ping 1,FAN Yi-xu 1,LIANG Ming-ming 2,YU Fang-jie 1,JIANG Feng 1,LIANG Hong-ze 1*.Investigation: Bromination of 2,6-Dimethoxypyridine[J].Journal of Ningbo University(Natural Science & Engineering Edition),2015,28(04):90-92.DOI:
| Title: | Investigation: Bromination of 2,6-Dimethoxypyridine |
| 作者: | 王君平 1, 樊一旭 1, 梁明明 2, 俞方杰 1, 江 峰 1, 梁洪泽 1* |
| Author(s): | WANG Jun-ping 1, FAN Yi-xu 1, LIANG Ming-ming 2, YU Fang-jie 1, JIANG Feng 1, LIANG Hong-ze 1* |
| 关键词: | 芳杂环化合物; 2,6-二甲氧基吡啶; 溴化反应 |
| Keywords: | aromatic heterocycles; 2,6-dimethoxy pyridine; bromination |
| 分类号: | O621.3 |
| 文献标识码: | A |
| 摘要: | 设计了2,6-二甲氧基吡啶溴代反应的新合成方法. 考察了在不同碱体系、反应温度、反应时间及反应浓度对一溴代产物收率的影响. 结果表明: 以外加有机碱作为缚酸剂, 可以使反应物充分释放, 提高产率; 新方法操作简单, 反应条件温和, 产率达75%以上, 与传统方法相当. |
| Abstract: | New synthetic method for the bromination of 2, 6-dimethoxypyridine is proposed. The influence of alkali system, temperature, reaction time and reactant concentration on the bromination of 2,6-dimethoxypydine is systematically investigated. The results show that with the addition of organic base as HBr scavenger more starting material is released, and the yield of product is thus increased. The new method features in practicality, simplicity, and convenience in handling. The yield can reach as high as 75%, which is compatible with that produced under traditional conditions. |
| 参考文献 /References: | [1] 慕长炜, 覃兆海. 吡啶类农药研究进展[J]. 现代农药, 2003, 2(2):1-6. [2] Garcia D V A, Martinez B V, Burgos C, et al. N-azinyl- pyridinium N-aminides: intermediates for the regioselective synthesis of 3-fluoro-2-amino pyridine derivatives[J]. Journal of Organic Chemistry, 1999, 64(3):1007-1010. [3] Stoit A R, den Hartog A P, Mons H, et al. 7-Azaindole derivatives as potential partial nicotinic agonists[J]. Bioorganic & Medicinal Chemistry Letters, 2008, 18(1): 188-193. [4] Abrahim A, Angelberger P, Kletter K, et al. Synthesis of fluorine-18-labeled 5- and 6-fluoro-2-pyridinamine[J]. Journal of Labelled Compounds and Radiopharmaceu- ticals. 2006, 49(4):345-356. [5] Scriven E F V, Toomey J E, Murugan R. Pyridine andpyridine derivatives, kirk-othmer encyclopedia of chemicaltechnology[M]. New York: Wiley Presses, 1996: 641-679. [6] Khanapure S P, Biehl E R. A Convenient synthesis of azaanthraquinones via polar addtion to hetaryne inter- midiates[J]. Heterocycles, 1988, 27(11):2643-2650. [7] Ca?ibano V, Rodríguez J F, Santos A, et al. Mild regioselective halogenation of activated pyridines with N-bromosuccinimide[J]. Synthesis, 2001, 38:2175-2179. [8] Pai C C, Lin C W, Lin C C, et al. Highly effective chiral dipyridylphosphine ligands: synthesis, structural determi- nation, and applications in the Ru-catalyzed asymmetric hydrogenation reactions[J]. Journal of the American Chemical Society, 2000, 122(46):11513-11514. [9] 刘洁, 王越, 齐艳, 等. 烷氧基卤代吡啶及其二苯基膦衍生物的合成研究[J]. 化学试剂, 2007, 29(4):193-196. [10] Chen Y Y, Shao H F, Wang Y S, et al. Regioselective ortho-lithiation of of halopyridines and synthesis of 3- bromo-2,6-dimethoxy-4-diphenylphosphino pyridines[J]. Journal of the Chinese Chemical Society, 2004, 12:17-19. |
| 备注/Memo: | 收稿日期: 2014-04-24. 宁波大学学报(理工版)网址: http://journallg.nbu.edu.cn/ 基金项目: 国家自然科学基金(51303108); 宁波市社会发展重点择优科技项目(2012C5002); 财政部、国家海洋局海洋经济创新发展区域示范成果转化及产业化项目. 第一作者: 王君平(1989-), 女, 陕西西安人, 在读硕士研究生, 主要研究方向: 合成及分析化学. E-mail: wangjunping@mail.nbu.edu.cn *通信作者: 梁洪泽(1964-), 男, 安徽马鞍山人, 博士/教授, 主要研究方向: 合成化学. E-mail: lianghongze@nbu.edu.cn 宁波大学学报(理工版)网址:http://journallg.nbu.edu.cn/ |