2-甲氧基-35-二硝基-6-叠氮基吡嗪的合成

兵工学报 ›› 2010, Vol. 31 ›› Issue (10): 1357-1362.

2-甲氧基-35-二硝基-6-叠氮基吡嗪的合成

刘耀鹏¹，陈华雄²，陈树森²，金韶华²

（1.陕西国防工业职业技术学院, 陕西西安 710302; 2. 北京理工大学材料科学与工程学院, 北京 100081)

收稿日期:2009-07-29 修回日期:2009-07-29 上线日期:2014-05-04
通讯作者: 刘耀鹏 E-mail:lyp42792@163.com
作者简介:刘耀鹏(1963—)，男，副教授

Synthesis of 2-methoxy-35-dinitryl-6-azidepyrazine

LIU Yao-peng¹, CHEN Hua-xiong², CHEN Shu-sen², JIN Shao-hua²

(1.Department of Chemical Engineering, Shaanxi Institute of Technology, Xi’an 710302， Shaanxi， China;2.College of Materials Science and Engineering , Beijing Institute of Technology , Beijing 100081, China)

Received:2009-07-29 Revised:2009-07-29 Online:2014-05-04
Contact: LIU Yao-peng E-mail:lyp42792@163.com

摘要/Abstract

摘要： 2-甲氧基-3,5-二硝基-6-叠氮基吡嗪(MDNAP)是一种新型含能化合物的母体，以2,6-二氯吡嗪为原料，经过甲氧基化合成得到2-甲氧基-6-氯吡嗪(MCP)，得率81%. 用硝硫混酸硝化MCP，在较温和的条件下得到2-甲氧基-3,5-二硝基-6-氯吡嗪(MDNCP)，得率75%. MDNCP经叠氮化合成得到MDNAP，得率60%，各中间体均用IR、H¹NMR、ESI-MS和EI-MS进行表征。

关键词: 有机化学, 2-甲氧基-3

Abstract: MDNAP is a precursor for novel energetic compounds. 2-methoxy-6-chlorin pyrazine (MCP) was first synthesized from raw material 2,6-dichlorin pyrazine by substituting chlorine with methoxyl with a yield of 81%. 2-methoxy-3,5-dinitryl-6-chlorin pyrazine (MDNCP) was obtained by the nitration of MCP with mixed nitric and sulfuric acids under facile conditions with a yield of 75%. 2-methoxy -3,5-dinitryl-6-azide pyrazine (MDNAP) was synthesized from MDNCP by the zaide substitution of MDNCP with a yield of 60%. Therein, all the intermediates were characterized by IR, H₁ NMR, ESI-MS and EI-MS.

Key words: organic chemistry, 2-methoxy-3,5-dinitryl-6-azidepyrazine, pyrazine, azide substitution, nitration

中图分类号:

TB34

刘耀鹏，陈华雄，陈树森，金韶华. 2-甲氧基-35-二硝基-6-叠氮基吡嗪的合成[J]. 兵工学报, 2010, 31(10): 1357-1362.

LIU Yao-peng, CHEN Hua-xiong, CHEN Shu-sen, JIN Shao-hua. Synthesis of 2-methoxy-35-dinitryl-6-azidepyrazine[J]. Acta Armamentarii, 2010, 31(10): 1357-1362.

参考文献

［1］王艳飞, 欧育湘, 刘进全，等. 7-氨基-6-硝基苯并二氧化呋咱的合成研究[J]. 化学世界, 2006, 47 (8): 484-486.
WANG Yan-fei, OU Yu-xiang, LIU Jin-quan, et al. Synthesis of 7-Amino-6-nitrobenzodifuroxan[J]. Chemical World, 2006, 47(8): 484-486. (in Chinese)
［2］姚超英. 离子色谱法测定沙坦类药物中的叠氮酸根[J]. 浙江大学学报，2008,35(3):305-307.
YAO Chao-ying. Determination orazideinsartanby ion chromatography[J]. Journal Zhejiang University, 2008, 35(3): 305-307. (in Chinese)
［3］颜范勇,陈立功,闫喜龙. 罗丹明类荧光染料的合成及应用[J]. 化学进展, 2006,18(3):252-261.
YAN Fan-yong,CHEN Li-gong,YAN Xi-long. Synthesis and applications of rhodamine fluorescent dyes[J]. Progress in Chemistry, 2006,18(3):252-261. (in Chinese)
［4］严曼, 石德清. N-（4，6-二取代嘧啶-2-基）-N-[1-（杂芳基）甲基-5-甲基-1H-1，2,3-三唑基-4-甲酰基]硫脲的合成与除草活性研究[J]. 有机化学, 2008,28(4): 736-740.
YAN Man, SHI De-qing. Synthesis and herbicidal activity of N-(4,6-Disubstituted pyrimidin2-yl)-N′-[1-(heteroaryl) methyl-5-methyl-1 H-1,2,3-triazol-4-ylcarbonyl]thiourea[J]. Chinese Journal of Organic Chemistry, 2008,28(4): 736-740. (in Chinese)
［5］刘进全,陈树森,欧育湘. 1-氧-2,6-二氨基-3,5-二硝基吡嗪(LLM-105)的合成[J]. 化学通报, 2006, 6(2): 151-153.
LIU Jin-quan, CHEN Shu-sen, OU Yu-xiang. Synthesis of 2, 6-Diamino-3,5-dinitropyrazing-1- oxide (LLM-105)[J]. Chemistry, 2006, 6(2): 151-153. (in Chinese)
［6］雷永鹏,徐松林, 阳世清. 吡唑及吡嗪类含能化合物研究进展[J]. 化学研究, 2007,18(2):107-112.
LEI Yong-peng, XU Song-lin, YANG Shi-qing. Advance in energetic compounds derived from pyrazole and pyrazine[J]. Chemical Resreach, 2007,18(2):107-112. (in Chinese)
［7］吕连营, 王建龙, 常永芳. 7-氨基-6-硝基苯并二氧化呋咱合成新方法[J]. 含能材料, 2006,14(6): 436-438.
L Lian-ying, WANG Jian-long, CHANG Yong-fang. New method for synthesis of 7-amino-6-nitrobenzodifuroxan[J]. Chinese Journal of Energetic Materials, 2006, 14(6): 436-438. (in Chinese)
［8］潘英明, 张业, 王恒山. 一些新型呋咱衍生物的合成[J]. 有机化学, 2006, 26(3): 314-317.
PAN Ying-ming, ZHANG Ye, WANG Heng-shan. Synthesis of some novel furazan derivatives[J]. Chinese Journal of Organic Chemistry, 2006, 26(3): 314-317. (in Chinese)
［9］欧育湘, 周智明. 炸药合成化学[M]. 北京：兵器工业出版社, 1998.
OU Yu-xiang, ZHOU Zhi-ming. Synthesis chemistry of explosives[M]. Beijing: The Publishing House of Ordnance Industry, 1998. (in Chinese)
［10］李战雄, 唐松青, 刘金涛. 3-氨基-4-(叠氮乙酰胺基) 呋咱合成[J]. 含能材料, 2002, 10(3): 112-113.
LI Zhan-xiong, TANG Song-qing, LIU Jin-tao. Synthesis of 3-amino-4-(azidoacetamido) furazan[J]. Chinese Journal of Energetic Materials, 2002, 10(3): 112-113. (in Chinese)
［11］盛涤伦, 马凤娥. 新型起爆药DACP的合成及其主要性能[J]. 含能材料, 2006, 14(3): 161-164.
SHENG Di-lun, MA Feng-e. Synthesis and main properties of new initiating explosive DACP[J]. Chinese Journal of Energetic Materials, 2006, 14(3): 161-164. (in Chinese)
［12］胡焕性, 张志忠, 赵凤起，等. 高能量密度材料3,4-二硝基呋咱基氧化呋咱性能及应用研究［J］. 兵工学报. 2004,25(2): 15-19.
HU Huan-xing, ZHANG Zhi-zhong, ZHAO Feng-qi, et al. A study on the properties and application of high energy density material DNTF[J]. Acta Armamentarii, 2004, 25(2): 15-19. (in Chinese)
［13］彭银. 多氯代多环芳烃的质谱裂解规律[J]. 质谱学报, 2009, 30(1):12-17.
PENG Yin. The fragmentation patters of polychlorinated polycyclic aromatic hydrocarbons[J]. Journal of Chinese Mass Spectrometry Society, 2009, 30(1): 12-17. (in Chinese)
［14］李馨，王英武，顾景凯，等. 三唑仑苯二氮磷类药物的电喷雾质谱裂解特征[J]. 分析化学, 2003,31(9): 1105-1108.
LI Xin, WANG Ying-wu; GU Jing-kai, et al. Fragmentation behaviors of triazolobenzodiazepines by electrospray ionization/quadrupole time-of-flight mass spectrometry[J]. Chinese Journal of Analytical Chemistry, 2003,31(9): 1105-1108. (in Chinese)
［15］洪爱华，尹平河，梁志红. 高效液相色谱-质谱联用法测定饮用水中的五氯苯酚[J]. 生态环境学报, 2010, 19(1): 69-71.
HONG Ai-hua, YIN Ping-he, LIANG Zhi-hong. Determination of pentachlorophenol in the tap water by liquid chromato graphy-tandem mass spectrometry[J]. Ecology and Environmental Sciences, 2010, 19(1): 69-71. (in Chinese)

[1]	张学梅, 董海山, 周智明, 李海华. 苦味酸氨化产物的合成及其性能研究[J]. 兵工学报, 2010, 31(10): 1341-1345.
[2]	陈甫雪，付占达，刘保杰，吴玉凯，周智明. 1-氨基-123-三唑的替代亲核取代反应研究[J]. 兵工学报, 2010, 31(10): 1389-1393.
[3]	陈树森，束庆海，金韶华,史彦山. 四乙酰基ニ甲酰基六氮杂异伍兹烷的硝解杂质与硝解机理[J]. 兵工学报, 2007, 28(1): 20-22.
[4]	刘进全，欧育湘，王艳飞，孟征，吴相国. 六硝基六氮杂异伍兹烷中杂质的结构表征及热分解研究[J]. 兵工学报, 2007, 28(1): 122-124.
[5]	刘进全，欧育湘. 六氮杂异伍兹烷衍生物的合成研究[J]. 兵工学报, 2006, 27(5): 920-923.
[6]	1:戴荣继,居恒宇, 顾峻岭, 张子青;2:杨荣杰,佟斌. 多乙烯多胺类多硝酸盐的合成及热性能测试[J]. 兵工学报, 2004, 25(4): 503-505.