[1]张雪利,林志兰,胡惠玲,等.微波辐射一步合成嘧啶并[4,5-b]喹啉衍生物[J].深圳大学学报理工版,2013,30(No.6(551-660)):636-642.[doi:10.3724/SP.J.1249.2013.06636]
 Zhang Xueli,Lin Zhilan,Hu Huiling,et al.Microwave-assisted one-pot synthesis of pyrimido[4,5-b]quinolines derivatives[J].Journal of Shenzhen University Science and Engineering,2013,30(No.6(551-660)):636-642.[doi:10.3724/SP.J.1249.2013.06636]
点击复制

微波辐射一步合成嘧啶并[4,5-b]喹啉衍生物()
分享到:

《深圳大学学报理工版》[ISSN:1000-2618/CN:44-1401/N]

卷:
第30卷
期数:
2013年No.6(551-660)
页码:
636-642
栏目:
材料科学
出版日期:
2013-09-30

文章信息/Info

Title:
Microwave-assisted one-pot synthesis of pyrimido[4,5-b]quinolines derivatives
文章编号:
20130614
作者:
张雪利林志兰胡惠玲贺佳欣高原
深圳大学化学与化工学院,深圳518060
Author(s):
Zhang Xueli Lin Zhilan Hu Huiling He Jiaxin and Gao Yuan
College of Chemistry and Chemical Engineering, Shenzhen University, Shenzhen 518060, P.R.China
关键词:
嘧啶并[45-b]喹啉微波辐射三组分缩合一锅法合成结构表征晶体结构
Keywords:
pyrimido[45-b]quinoline microwave irradiation three-component reaction one-pot synthesis structural characterization crystal structure
分类号:
O 626.411
DOI:
10.3724/SP.J.1249.2013.06636
文献标志码:
A
摘要:
以醛、嘧啶酮衍生物和环己二酮类化合物为原料,在少量乙二醇中,经微波辐射合成了两个系列嘧啶并[4,5-b]喹啉衍生物.研究发现,其最佳反应条件为:微波功率480 W,反应温度85 ℃,辐射反应时间6~9 min.结果表明,该方法不仅适用于带有推电子基团或拉电子基团的芳香醛,也适用于杂环醛.产物的结构经红外光谱、核磁共振氢谱和元素分析表征,同时用X射线衍射法研究了化合物1d的晶体结构.
Abstract:
Two series of pyrimido[4,5-b]quinolone derivatives were synthesized via the reaction of aldehydes with pyrimidiones and 1, 3-cyclohexanediones in ethylene glycol under microwave irradiation. The optimum reaction conditions were as follows: microwave power 480 W, reaction temperature 85 ℃ and irradiation time 6-9 min. This method is applicable not only to aromatic aldehydes with electron donating group or electron withdrawing groups but also to heterocyclic aldehydes. The structures of the products were identified by infrared spectroscopy (IR), H-nuclear magnetic resonance spectroscopy (1HNMR) spectra and elemental analysis. The structure of 1d was further confirmed by X-ray single crystallography.

参考文献/References:

[1] Krishnamurthy B, Vinaya K, Rakshith D, et al. Synthesis of 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one derivatives as antibacterial agents[J]. Medicinal Chemistry, 2013, 9(2): 240-248.
[2] Kurumurthy C, Rao P S, Swamy B V, et al. Synthesis of novel alkyltriazole tagged pyrido[2,3-d]pyrimidine derivatives and their anticancer activity[J]. European Journal of Medicinal Chemistry, 2011, 46(8): 3462-3468.
[3] Bhargava S, Rajwanshi L K. Synthesis of some novel pyrido[2,3-d]pyrimidine derivatives and their antimicrobial investigations[J]. Indian Journal of Chemistry Section B:Organic Chemistry Including Medicinal Chemistry, 2013, 52(3): 448-452.
[4] Liu Jianchao, He Hongwu, Chen Helian. Synthesis and fungicidal activities of 2-(amino/acetoxy)-3-(4-methylphenyl)-thieno[3′,2′:5,6]pyrido[4,3-d]-pyrimidin-4(3H)-one derivatives[J]. Chinese Journal of Organic Chemistry, 2011, 31(8): 1208-1212.(in Chinese)
刘建超,贺红武,陈荷莲. 2-氨基(芳氧基)-3-对甲基苯基噻吩并[3′,2′:5,6]吡啶并[4,3-d]嘧啶-4(3H)-酮的合成和生物活性[J]. 有机化学,2011, 31(8): 1208-1212.
[5] Farghaly T A, Hassaneen H M E. Synthesis of pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5-ones as potential antimicrobial agents[J]. Archives of Pharmacal Research, 2013, 36(5): 564-572.
[6] Ren Qingyun, He Hongwu, Liu Jianchao. Synthesis, crystal structure and fungicidal activity of tetrahydrobenzo[4′,5′]thieno[3′,2′:5,6]pyrido[4,3-d]pyrimidin-4(3H)-one derivatives[J]. Chinese Journal of Organic Chemistry, 2007, 27(3): 397-401.(in Chinese)
任青云,贺红武,刘建超. 四氢苯并[4′,5′]噻吩并[3′,2′:5,6]吡啶并[4,3-d]嘧啶-4(3H)-酮的合成、晶体结构及杀菌活性[J]. 有机化学,2007, 27(3): 397-401.
[7] Wang Daolin, Yu Jiayi, Li Wei, et al. Synthesis of naphthylazuleno[2,1-d]pyrimidin-4-amines[J]. Chinese Journal of Organic Chemistry, 2012, 32: 1547-1551.(in Chinese)
王道林,于家懿,李伟,等. 萘基薁并[2,1-d]嘧啶-4-胺类衍生物的合成[J]. 有机化学,2012, 32: 1547-1551.
[8] Bishnoi A, Singh S, Tiwari A K, et al. Synthesis, characterization and biological activity of new cyclization products of 3-(4-substituted benzylidene)-2H-pyrido[1,2-a]pyrimidine 2,4-(3H)-diones[J]. Journal of Chemical Sciences, 2013, 125(2): 305-312.
[9] El-Gazzar A R, Hafez H N, Nawwar G A M. New acyclic nucleosides analogues as potential analgesic, anti-inflammatory, anti-oxidant and anti-microbial derived from pyrimido[4,5-b]quinolines[J]. European Journal of Medicinal Chemistry, 2009, 44(4): 1427-1436.
[10] Parameswaran K, Sivaguru P, Lalitha A. Synthesis of novel bis(pyrimido[5,4-c]quinoline-2,4(1H,3H)-dione) and its derivatives: evaluation of their antioxidant properties[J]. Bioorganic & Medicinal Chemistry Letters, 2013, 23(13): 3873-3878.
[11] Alqasoumi S I, Al-Taweel A M, Alafeefy A M, et al. Novel quinolines and pyrimido[4,5-b]quinolines bearing biologically active sulfonamide moiety as a new class of antitumor agents[J]. European Journal of Medicinal Chemistry, 2010, 45(2):738-744.
[12] Dou X X, Tao L, Hu C Q, et al. Synthesis and biological evaluation of novel pyrimido[4,5-b]quinoline-2,4-dione derivatives as MDM2 ubiquitin ligase inhibitors[J]. Medicinal Chemistry, 2013, 9(4):581-587.
[13] El-Gazzar A R, El-Enany M M, Mahmoud M N. Synthesis, analgesic, anti-inflammatory, and antimicrobial activity of some novel pyrimido[4,5-b]quinolin-4-ones [J]. Bioorganic & Medicinal Chemistry, 2008, 16(6): 3261-3273.
[14] El-Shafei A, Fadda A A, Bondock S, et al. Facile Synthesis, Pure DFT Calculations, and PM3 Semiempirical MO Method Validation of Regiospecificity of Novel 1,4-Dihydropyrido[2,3-d]pyrimidine Derivatives[J]. Synthetic Communications, 2010, 40(18): 2788-2805.
[15] Pang Yan, Lu Weizhong, Wang Fang, et al. Synthesis and characterization of 1,3-di(2′-benzimidazole)benzene under microwave irradiation[J]. Journal of Shenzhen University Science and Engineering, 2009, 26(2): 193-196.(in Chinese)
逄艳, 吕维忠, 王芳, 等. 1,3-双(2′-苯并咪唑基)苯的微波合成及表征[J]. 深圳大学学报理工版,2009, 26(2): 193-196.
[16] Obert T G,Mercedes M S. Structure and properties of poly(benzyl acrylate) synthesizes under microwave energy[J].Radiation Physics and Chemistry, 2008,77(5): 597-604.
[17] Bose A K, Manhas M S, Ganguly S N, et al. More chemistry for less pollution: applications for process development[J]. Synthesis, 2002, 2002(11): 1578-1591.
[18] Kavinchan J, Thongtem T, Thongtem S. Cyclic microwave assisted synthesis of Sb2S3 dumb-bells using polyvinylpyrrolidone as a template and splitting agent[J]. Materials Letters, 2010, 64(21): 2388-2391.
[19] Tu Shujiang, Fang Fang, Li Tuanjie, et al. An efficient one-pot synthesis of novel pyrimidoquinoline derivatives under microwave irradiation without catalyst[J]. Journal of Heterocyclic Chemistry, 2005, 42(4): 707-710.

备注/Memo

备注/Memo:
Received:2011-11-21;Revised:2013-04-03;Accepted:2013-06-20
Foundation:National Natural Science Foundation of China (81071144); Natural Science Foundation of Guangdong Province(9451806001002961)
Corresponding author:Professor Gao Yuan. E-mail: szgaoy@tom.com
Citation:Zhang Xueli, Lin Zhilan, Hu Huiling, et al. Microwave-assisted one-pot synthesis of pyrimido[4, 5-b]quinolines derivatives[J]. Journal of Shenzhen University Science and Engineering, 2013, 30(6): 636-642.(in Chinese)
基金项目:国家自然科学基金资助项目(81071144);广东省自然科学基金资助项目(9451806001002961)
作者简介:张雪利(1965-),男(汉族),浙江省杭州市人,深圳大学副教授、博士.E-mail: zhangxueli5@yahoo.com.cn
引文:张雪利,林志兰,胡惠玲,等. 微波辐射下一步合成嘧啶并[4,5-b]喹啉衍生物[J]. 深圳大学学报理工版,2013,30(6):636-642.
更新日期/Last Update: 2013-11-20