Synthesis of 5-Amino-2-oxo-7-aryl-2,3,4,7-tetrahydro-1,3-thiazolo[4,5-b]pyridine-6-carboxamide Derivatives under Microwave Irradiation

doi:10.6023/cjoc201304037

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (10): 2220-2225.DOI: 10.6023/cjoc201304037 Previous Articles Next Articles

5-胺基-2-氧代-7-芳基-2,3,4,7-四氢-1,3-噻唑并[4,5-b]吡啶-6-甲酰胺类化合物的微波合成

孙宏顺^a,b, 王建强^a, 郭成^a, 沈临江^a

a 南京工业大学理学院南京 211816;
b 南京化工职业技术学院化学工程系南京 210048

收稿日期:2013-04-23 修回日期:2013-05-28 发布日期:2013-07-03
通讯作者: 郭成, 沈临江 E-mail:guocheng@njut.edu.cn; ljshen@njut.edu.cn
基金资助:
国家自然科学青年基金(No. 21106069)、南京化工职业技术学院院级重点(No. NHKY-2013-2)资助项目

Synthesis of 5-Amino-2-oxo-7-aryl-2,3,4,7-tetrahydro-1,3-thiazolo[4,5-b]pyridine-6-carboxamide Derivatives under Microwave Irradiation

Sun Hongshun^a,b, Wang Jianqiang^a, Guo Cheng^a, Shen Linjiang^a

a Nanjing University of Technology, Nanjing 211816;
b Nanjing College of Chemical Technology, Nanjing 210048

Received:2013-04-23 Revised:2013-05-28 Published:2013-07-03
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21106069) and the Key Program of Nanjing College of Chemical Technology (No. NHKY-2013-2).

Five new 5-amino-2-oxo-7-aryl-2,3,4,7-tetrahydro-1,3-thiazolo[4,5-b]pyridine-6-carboxamide derivatives, which are different with the products of 5-amino-2-oxo-7-aryl-2,3,4,7-tetrahydro-1,3-thiazolo[4,5-b]pyridine-6-carbonitrile derivatives in the conventional heating conditions, were synthesized by using arylmethylene malononitrile, 2,4-thiazolidinedione and ammonium acetate in one-pot via microwave irradiation techniques. And the reaction mechanism was discussed. The structures of these compounds were characterized by ¹H NMR, IR, MS and elemental analysis.

Key words: 2,4-thiazolidinedione, thiazolo[4,5-b]pyrirnidine, microwave irradiation, synthesis

Cite this article

Sun Hongshun, Wang Jianqiang, Guo Cheng, Shen Linjiang. Synthesis of 5-Amino-2-oxo-7-aryl-2,3,4,7-tetrahydro-1,3-thiazolo[4,5-b]pyridine-6-carboxamide Derivatives under Microwave Irradiation[J]. Chin. J. Org. Chem., 2013, 33(10): 2220-2225.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Gao, Y.; Tu, S.-J.; Li, T.-J.; Zhang, X.-J.; Zhu, S.-L.; Fang, F.; Shi, D.-Q. Synth. Commun. 2004, 34, 1295.
[2] Hamrlin, J.; Benhaoua, H.; Kasm, S. Tetrahedron Lett. 1998, 39, 8093.
[3] Huang, H.-M.; Yu, H.-T.; Chen, P.-L.; Han, J.; Meng, J.-B. Chin. J. Org. Chem. 2004, 24, 502 (in Chinese). (黄华鸣, 于海涛, 陈培丽, 韩杰, 孟继本, 有机化学, 2004, 24, 502.)
[4] Jeselnik, M.; Varma, R. S.; Polanc, S.; Kocevar, M. Green Chem. 2002, 4, 35.
[5] Wang, J.; Jiang, F.-C. Chin. J. Org. Chem. 2002, 22, 212 (in Chinese). (王静, 姜风超, 有机化学, 2002, 22, 212.)
[6] Wheeler, G. P.; Bowdon, B. J.; Werline, J. A.; Adamson, D. J.; Temple, C. G. Cancer Res. 1982, 42, 791.
[7] Mu, C.-W.; Tan, C.-H. Modern Agrochem. 2003, 2, 1 (in Chinese). (慕长炜, 覃兆海, 现代农药, 2003, 2, 1.)
[8] Xu, X.-Y.; Chen, G.; Qian, X.-H. Chin. J. Pestic. Sci. 2003, 5, 1 (in Chinese). (徐晓勇, 陈刚, 钱旭红, 农药学学报, 2003, 5, 1.)
[9] Tu, S.-J.; Zhang, Q.-S. J. Xuzhou Normal Univ. 2006, 24, 1 (in Chinese). (屠树江, 张前上, 徐州师范大学学报, 2006, 24, 1.)
[10] Cui, S.-F.; Wang, Y.; Lv, J.-S.; Damu Guri, L. V.; Zhou, C.-H. Sci. Sin. Chim. 2012, 42, 1105 (in Chinese).(崔胜峰, 王艳, 吕敬松, Damu Guri, L. V., 周成合, 中国科学: 化学, 2012, 42, 1105.)
[11] Yoshioka, T.; Fujita, T.; Kanai, T. J. Med. Chem. 1989, 32, 421.
[12] Lei, Q.; Guang, B.; Wang, L.-B. J. Sichuan Univ. 2003, 35, 107 (in Chinese). (雷琴, 广兵, 王良兵, 四川大学学报, 2003, 35, 107.)
[13] Lu, X.-P. Prog. Pharm. Sci. 2000, 24, 122 (in Chinese). (陆效平, 药学进展, 2000, 24, 122.)
[14] Sohda, T.; Mizuno, K.; Imamiya, E. Chem. Pharm. Bull. 1982, 30, 3580.
[15] Heng, X.-P.; Yang, L.-Q.; Zhou, G.-Y. Chin. J. Rural Med. Pharm. 2006, 13, 43 (in Chinese). (衡先培, 杨柳清, 周国英, 中国乡村医药杂志, 2006, 13, 43.)
[16] Bacani, G. M.; Broggini, D.; Cheung, E. Y.; Chrovian, C. C.; Deng, X.; Fourine, A. M.; Gomez, L.; Grice, C. A.; Kearney, A. M.; Landry-Bayle, A. M.; Lee-Dutra, A.; Liang, J. T.; Lochner, S.; Mani, N. S.; Santillan, A.; Sappey, K. C.; Sepassi, K.; Tanis, V. M.; Wickboldt, A. T.; Wiener, J. J. M.; Zinser, H. CN 102056933, 2009[Chem. Abstr. 2009, 151, 470236].
[17] Cuccia, S.; Haley, G. J.; Barnes, K. D.; Wood, W. W.; Hu, Y.; Cotter, H. V. T.; Gypser, A.; Schwoegler, A. CN 1553773, 2004[Chem. Abstr. 2005, 138, 106691].
[18] Jones, C. D.; Luke, R. W. A.; Mccoull, W. CN 1942475, 2007[Chem. Abstr. 2007, 143, 211925].
[19] Gallardo-Godoy, A. CN 101827593, 2010[Chem. Abstr. 2010, 150, 352134].
[20] Bemis, J.; Disch, J. S.; Ng, P. Y.; Oalmann, C.; Perni, R. B.; Vu, C. B. CN 101801981, 2010[Chem. Abstr. 2010, 150, 77670].
[21] Rao, V. S.; S. V. S.; Arun, K. G. Asian J. Chem. 2000, 12, 286．
[22] Zhang, Y.-L.; Zhou, Z.-Q. Org. Chem. Internt. 2012, 2012, 1.
[23] Yang, D.-C.; Yan, J.-F.; Zhang, K. Cheng, X. CN 102731429, 2012[Chem. Abstr. 2012, 157, 663015].

5-胺基-2-氧代-7-芳基-2,3,4,7-四氢-1,3-噻唑并[4,5-b]吡啶-6-甲酰胺类化合物的微波合成

Synthesis of 5-Amino-2-oxo-7-aryl-2,3,4,7-tetrahydro-1,3-thiazolo[4,5-b]pyridine-6-carboxamide Derivatives under Microwave Irradiation

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[3]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[4]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[7]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[8]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[9]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[10]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[11]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[12]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[15]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.