[1]刘玮炜,霍云峰,张强,等.2-氨基-5-甲氧基苯基-1,3,4-噻二唑的合成[J].华侨大学学报(自然科学版),2013,34(5):539-541.[doi:10.11830/ISSN.1000-5013.2013.05.0539]
 LIU Wei-wei,HUO Yun-feng,ZHANG Qiang,et al.Synthesis of 2-Amino-5-Methoxylphenyl-1,3,4-Thiadiazole[J].Journal of Huaqiao University(Natural Science),2013,34(5):539-541.[doi:10.11830/ISSN.1000-5013.2013.05.0539]
点击复制

2-氨基-5-甲氧基苯基-1,3,4-噻二唑的合成()
分享到:

《华侨大学学报(自然科学版)》[ISSN:1000-5013/CN:35-1079/N]

卷:
第34卷
期数:
2013年第5期
页码:
539-541
栏目:
出版日期:
2013-09-20

文章信息/Info

Title:
Synthesis of 2-Amino-5-Methoxylphenyl-1,3,4-Thiadiazole
文章编号:
1000-5013(2013)05-0539-03
作者:
刘玮炜12 霍云峰1 张强1 龚峰1 吴杨全1
1. 淮海工学院 制药工程系, 江苏 连云港 222005;2. 江苏省海洋资源开发研究院, 江苏 连云港 222005
Author(s):
LIU Wei-wei12 HUO Yun-feng1 ZHANG Qiang1 GONG Feng1 WU Yang-quan1
1. Department of Pharmaceutical Engineering, Huaihai Institute of Technology, Lianyungang 222005, China; 2. Jiangsu of Marine Resources, Lianyungang 222005, China
关键词:
2-氨基-5-甲氧基苯基-134-噻二唑 热反应 微波加热 三氯氧磷
Keywords:
2-amino-5-methoxylphenyl-134-thiadiazole thermal reaction microwave-assisted synthesis phosphorous oxychloride
分类号:
O626.27
DOI:
10.11830/ISSN.1000-5013.2013.05.0539
文献标志码:
A
摘要:
在三氯氧磷存在下, 以甲氧基苯甲酸、氨基硫脲为原料, 通过直接加热和微波加热两种方式, 合成3个2-氨基-5-取代基-1,3,4噻二唑. 通过优化工艺条件, 得到传统热反应最佳条件,即反应温度为75 ℃, 反应时间为4 h, 三氯氧磷与酸的摩尔比为4∶1,所得产物经熔点测试、红外光谱和核磁共振氢谱进行了确认.
Abstract:
In the presence of phosphorus oxychloride, three kinds of 2-amino-5-methoxylphenyl-1,3,4-thiadiazoles have been synthesized from methoxybenzoic acid and thiosemicarbazide under direct heating and microwave-assisted heating conditions. Through optimizing the reaction conditions, we concluded the ideal conditions for direct heating: the temperature is 75 ℃, the reaction time is 4 h, and the mole ratio of phosphorus oxychloride and acid is 4∶1. The obtained products have been characterized by melting point, FT-IR and 1H NMR.

参考文献/References:

[1] RESKI W,MATYSIAKB J,KABDEFER-SZERSZEN M.Anticancer,neuroprotective activities and computational studies of 2-amino-1,3,4-thiadiazole based compound[J].Bioorg Med Chem,2007,15(9):3201-3207.
[2] FERRARI S,MORANDI F,MOTIEJUNAS D,et al.Virtual screening identification of nonfolate compounds,including a CNS drug, as antiparasitic agents inhibiting pteridine reductase[J].J Med Chem,2011,54(1):211-221.
[3] KIDWAI M,MISRA P,KUMAR R,et al.Microwave assisted synthesis and antibacterial activity of new quinolone derivatives[J].Montash.Chem,1998,129(8/9):961-965.
[4] JATAV V,KASHAW S,MISHRA P.Synthesis, antibacterial and antifungal activity of some novel 3-[5-(4-substituted phenyl)1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones[J].Med Chem Res,2008,17(2):169-181.
[5] CHOHAN Z H,PERVEZ H,RAUF A,et al.Antibacterial role of SO2-4,NO3-,C2O42- and CH3CO2- anions on Cu(Ⅱ)and Zn(Ⅱ)complexes of a thiadiazole-derived pyrrolyl schiff base[J].Metal Based Drugs,2002,8(5):263-267.
[6] MAZZONE G,PIGNATELLO R,MAZZONE S,et al.Synthesis and local anesthetic activity of alkylaminoacyl derivatives of 2-amino-1,3,4-thiadiazole[J].Farmaco,1993,48(9):1207-1224.
[7] CRESSIER D,PROUILLAC C,HERNANDEZ P,et al.Synthesis, antioxidant properties and radioprotective effects of new benzothiazoles and thiadiazoles[J].Bioorg Med Chem,2009,17(14):5275-5284.
[8] 陈峙,钟炜东,张亚娟.药物中间体3,5-二甲氧基苯甲醛的合成[J].医学信息,2011(8):4204-4205.
[9] 杜海军,杜海堂,桑维钧,等.3-(3,4,5-三甲氧基苯基)-4-氨基-5-取代苄巯基-1,2,4-三唑的合成及其生物活性[J].合成化学,2012,20(1):76-79.
[10] 韩锋,万嵘,王瑶,等.1,3,4-噻二唑基芳酰基脲的合成和生物活性[J].有机化学,2010,30(1):132.
[11] TU Guo-gang,LI Shao-hua,HUANG Hui-ming,et al.Novel aminopeptidase N inhibitors derived from 1,3,4-thiadiazole scaffold[J].Bioorg Med Chem,2008,16(14):6663-6668.
[12] HILFKER M A,WANG Ning,HOU Xiao-ping,et al.Discovery of novel aminothiadiazole amides as selective EP3 receptor antagonists[J].Bioorg Med Chem Lett,2009,19(15):4292-4295.
[13] ZHENG Kai-bo,HE Jun,ZHANG Jie.Synthesis and antitumor activity of N1-acetylamino-(5-alkyl/aryl-1,3,4-thiadiazole-2-yl)-5-fluorouracil derivatives[J].Chin Chem Lett,2008,19(11):1281-1284.
[14] LI Zheng,YU Jin-lan,YANG Jing-ya,et al.Polymer-supported dichlorophosphate: A recoverable new reagent for synthesis of 2-amino-1,3,4-thiadiazoles[J].Chem Res,2005,36(43):341-343.
[15] YU Yu-ye.Microwave-assisted aynthesis and biological activity of 2,5-disubstituted-1,3,4-thiadiazole[J].Asian J Chem,2007,19(4):3141-3144.
[16] 刘玉婷,周瑛,尹大伟.2-氨基-5-芳基-1,3,4-噻二唑的合成[J].精细石油化工,2011,28(1):61-63.

相似文献/References:

[1]刘嘉川,程琳.2,3,6,7-四甲基三蝶烯的新型有效合成及表征[J].华侨大学学报(自然科学版),2012,33(5):518.[doi:10.11830/ISSN.1000-5013.2012.05.0518]
 LIU Jia-chuan,CHENG Lin.New Efficient Synthesis and Characterization of 2,3,6,7-Tetramethyltriptycene[J].Journal of Huaqiao University(Natural Science),2012,33(5):518.[doi:10.11830/ISSN.1000-5013.2012.05.0518]
[2]刘玮炜,吴杨全,龚峰,等.N-硝基苯甲酰基-1,3,4,6-四-O-乙酰基-2-脱氧-β-D-氨基葡萄糖的合成与表征[J].华侨大学学报(自然科学版),2013,34(1):56.[doi:10.11830/ISSN.1000-5013.2013.01.0056]
 LIU Wei-wei,WU Yang-quan,GONG Feng,et al.Synthesis and Characterization of N-Nitromaticacyl-1,3,4,6-Tetra-O-Acetyl-2-Deoxy-β-D-Glucopyranose[J].Journal of Huaqiao University(Natural Science),2013,34(5):56.[doi:10.11830/ISSN.1000-5013.2013.01.0056]
[3]胡素贞,肖子敬.二维铜配合物聚合物[Cu(MDNS)2]n的合成与表征[J].华侨大学学报(自然科学版),2013,34(4):404.[doi:10.11830/ISSN.1000-5013.2013.04.0404]
 HU Su-zhen,XIAO Zi-jing.Synthesis and Characterization of 2D Coordination Polymer [Cu(MDNS)2]n[J].Journal of Huaqiao University(Natural Science),2013,34(5):404.[doi:10.11830/ISSN.1000-5013.2013.04.0404]

备注/Memo

备注/Memo:
收稿日期: 2012-08-29
通信作者: 刘玮炜(1965-),女,教授,主要从事有机合成的研究.E-mail:liuww2007ly@yahoo.com.cn.
基金项目: 江苏省高校自然科学研究重大基金资助项目(10KJA170003); 江苏省高校科研成果产业化推进研究基金资助项目(JHB2012-60); 江苏省连云港市科技攻关项目(CG1105)
更新日期/Last Update: 2013-09-20