纳米金属氧化物催化含氮杂环类化合物的合成研究进展
收稿日期: 2016-09-06
修回日期: 2016-11-27
网络出版日期: 2016-12-12
基金资助
陕西省自然科学基础研究计划（No.2014JQ2064）、陕西省教育厅重点实验室项目（No.15JS012）、陕西科技大学博士科研启动基金（No.BJ12-26）资助项目.
Progress in the Synthesis of N-Fused Heterocycles Catalyzed by Nanocrystalline Metal Oxides
Received date: 2016-09-06
Revised date: 2016-11-27
Online published: 2016-12-12
Supported by
Project supported by the Natural Science Basic Research Plan in Shaanxi Province (No. 2014JQ2064), the Scientific Research Project Item for Key Laboratory of Shaanxi Provincal Education Department (No. 15JS012), and the Foundation for Young Scholars of Shaanxi University of Science & Technology (No. BJ12-26).
张金 , 刘佳 , 马养民 , 程佩 . 纳米金属氧化物催化含氮杂环类化合物的合成研究进展[J]. 有机化学, 2017 , 37(3) : 555 -565 . DOI: 10.6023/cjoc201609006
N-Fused heterocycles are an important class of organic compounds. As a basic scaffold of a wide variety of biologically active alkaloids and synthetic pharmaceuticals and agrochemicals, the construction methods of N-fused heterocycles have attracted much attention. Significant efforts have been devoted to the application of the nanocrystalline metal oxides as heterogeneous, efficient and environmentally friendly catalyst in organic reaction. This review provides a summary of the synthesis of the different kinds of N-fused heterocycles in recent 5 years catalyzed by the nanocrystalline metal oxides.
Key words： nanocrystalline metal oxides; N-fused heterocycles; catalyst
[1] Shafiee, A. Eur. J. Med. Chem. 2015, 97, 334.
[2] Rani, R.; Granchi, C. Eur. J. Med. Chem. 2015, 97, 505.
[3] Yang, R.; Gao, Z.-F.; Zhao, J.-Y.; Li, W.-B.; Zhou, L.; Miao, F. J. Agric. Food Chem. 2015, 63, 1906.
[4] Manivannan, E.; Chaturvedi, S. C. Bioorg. Med. Chem. 2011, 19, 4520.
[5] Giardina, D.; Martarelli, D.; Sagratini, G.; Angeli, P.; Ballinari, D.; Gulini, U.; Melchiorre, C.; Poggesi, E.; Pompei, P. J. Med. Chem. 2009, 52, 4951.
[6] Wermuth, C. G.; Schlewer, G.; Bourguignon, J. J.; Maghioros, G.; Bouchet, M. J.; Moire, C.; Kan, J. P.; Worms, P.; Biziere, K. J. Med. Chem. 1989, 32, 528.
[7] Rueda, L.; Castellote, I.; Castro-Pichel, J.; Chaparro, M. J.; de la Rosa, J. C.; Garcia-Perez, A.; Gordo, M.; Jimenez-Diaz, M. B.; Kessler, A.; Macdonald, S. J. F.; Martinez, M. S.; Sanz, L. M.; Gamo, F. J.; Fernandez, E. ACS Med. Chem. Lett. 2011, 2, 840.
[8] Wang, J.; Tan, H.; Li, Y.; Ma, Y.; Li, Z.; Guddat, L. W. J. Agric. Food Chem. 2011, 59, 9892.
[9] Hu Q. Z.; Qin Y; Xi H. T; Sun X. Q. Chin. J. Synth. Chem. 2011, 19, 480 (in Chinese).(胡泉子, 秦瑗, 席海涛, 孙小强, 合成化学, 2011, 19, 480.)
[10] Yang, W.; Chen, J.; Huang, X.; Ding, J.; Liu, M.; Wu, H. Org. Lett. 2014, 16, 5418.
[11] Ding, Z. W.; Tan, Q. T.; Liu, B. X.; Zhang, K.; Xu, B. Acta Chim. Sinica 2015, 73, 1302 (in Chinese).(丁正伟, 谭启涛, 刘秉新, 张可, 许斌, 化学学报, 2015, 73, 1302.)
[12] Zhao, J. B.; Zhang, Q. Acta Chim. Sinica 2015, 73, 1235 (in Chinese).(赵金钵, 张前, 化学学报, 2015, 73, 1235.)
[13] Zhang, Z. R.; Zheng, X. L.; Guo, C. B. Chin. J. Org. Chem. 2016, 36, 1241 (in Chinese).(张钊瑞, 郑晓霖, 郭长彬, 有机化学, 2016, 36, 1241.)
[14] Ji, Y. G.; Wu, L.; Fan, Q. H. Acta Chim. Sinica 2014, 72, 798 (in Chinese).(季益刚, 吴磊, 范青华, 化学学报, 2014, 72, 798.)
[15] Elwahy, A. H. M.; Shaaban, M. R. RSC Adv. 2015, 5, 75659.
[16] Teimouri, A.; Chermahini, A. N. Chin. J. Chem. 2012, 30, 372.
[17] Ma, F. P.; Li, P. H.; Li, B. L.; Mo, L. P.; Liu, N.; Kang, H. J.; Liu, Y. N.; Zhang, Z. H. Appl. Catal. A:Gen. 2013, 457, 34.
[18] Li, B.; Hu, H.; Mo, L.; Zhang, Z. RSC Adv. 2014, 4, 12929.
[19] Li, B.; Zhang, M.; Hu, H.; Du, X.; Zhang, Z. New J. Chem. 2014, 38, 2435.
[20] Sabbaghan, M.; Ghalaei, A. J. Mol. Liq. 2014, 193, 116.
[21] Hajinasiri, R.; Hossaini, Z.; Sheikholeslami-Farahani, F. Comb. Chem. High Throughput Screening 2015, 18, 42.
[22] Azgomi, N.; Mokhtary, M. J. Mol. Catal. A:Chem. 2015, 398, 58.
[23] Sobhani, S.; Honarmand, M. Appl. Catal. A:Gen. 2013, 467, 456.
[24] Eshghi, H.; Khojastehnezhad, A.; Moeinpour, F.; Rezaeian, S.; Bakavoli, M.; Teymouri, M.; Rostami, A.; Haghbeen, K. Tetrahedron 2015, 71, 436.
[25] Teimouri, A.; Chermahini, A. N. J. Mol. Catal. A:Chem. 2011, 346, 39.
[26] Safari, J.; Zarnegar, Z. J. Chem. Sci. 2013, 125, 835.
[27] Zarnegar, Z.; Safari, J. RSC Adv. 2014, 4, 20932.
[28] Reddy, B.; Vijayakumar, V.; Arasu, M.; Al-Dhabi, N. Molecules 2015, 20, 19221.
[29] Mitra, S.; Bagdi, A. K.; Majee, A.; Hajra, A. Tetrahedron Lett. 2013, 54, 4982.
[30] Zakerinasab, B.; Nasseri, M. A.; Hassani, H.; Samieadel, M. M. Res. Chem. Intermed. 2015, 42, 3169.
[31] Sangshetti, J. N.; Dharmadhikari, P. P.; Chouthe, R. S.; Fatema, B.; Lad, V.; Karande, V.; Darandale, S. N.; Shinde, D. B. Bioorg. Med. Chem. Lett. 2013, 23, 2250.
[32] Murty, M. S. R.; Penthala, R.; Buddana, S. K.; Prakasham, R. S.; Das, P.; Polepalli, S.; Jain, N.; Bojja, S. Med. Chem. Res. 2014, 23, 4579.
[33] Kamal, A.; Swapna, P. RSC Adv. 2013, 3, 7419.
[34] Salam, N.; Sinha, A.; Mondal, P.; Roy, A. S.; Jana, N. R.; Islam, S. M. RSC Adv. 2013, 3, 18087.
[35] Bhardwaj, M.; Jamwal, B.; Paul, S. Catal. Lett. 2016, 146, 629.
[36] Vahdat, S. M.; Raz, S. G.; Baghery, S. J. Chem. Sci. (Bangalore, India) 2014, 126, 579.
[37] Banerjee, S.; Payra, S.; Saha, A.; Sereda, G. Tetrahedron Lett. 2014, 55, 5515.
[38] Maleki, B.; Baghayeri, M.; Vahdat, S. M.; Mohammadzadeh, A.; Akhoondi, S. RSC Adv. 2015, 5, 46545.
[39] Shiraishi, Y.; Sugano, Y.; Tanaka, S.; Hirai, T. Angew. Chem., Int. Ed. 2010, 49, 1656.
[40] Karami, B.; Nikoseresht, S.; Khodabakhshi, S. Chin. J. Catal. 2012, 33, 298.
[41] Alinezhad, H.; Salehian, F.; Biparva, P. Synth. Commun. 2012, 42, 102.
[42] Santra, S.; Majee, A.; Hajra, A. Tetrahedron Lett. 2012, 53, 1974.
[43] Inamdar, S. M.; More, V. K.; Mandal, S. K. Tetrahedron Lett. 2013, 54, 579.
[44] Yang, D.; Zhu, X.; Wei, W.; Sun, N.; Yuan, L.; Jiang, M.; You, J.; Wang, H. RSC Adv. 2014, 4, 17832.
[45] Shelkar, R.; Sarode, S.; Nagarkar, J. Tetrahedron Lett. 2013, 54, 6986.
[46] Hajipour, A. R.; Khorsandi, Z.; Mortazavi, M.; Farrokhpour, H. RSC Adv. 2015, 5, 107822.
[47] Jamatia, R.; Saha, M.; Pal, A. K. RSC Adv. 2014, 4, 12826.
[48] Maleki, A.; Ghamari, N.; Kamalzare, M. RSC Adv. 2014, 4, 9416.
[49] Sharma, H.; Kaur, N.; Singh, N.; Jang, D. O. Green Chem. 2015, 17, 4263.
[50] Azizi, K.; Karimi, M.; Heydari, A. Tetrahedron Lett. 2015, 56, 812.
[51] Amoozadeh, A.; Azadeh, R. A.; Rahmani, S.; Salehi, M.; Kubicki, M.; Dutkiewicz, G. Phosphorus, Sulfur Silicon Relat. Elem. 2015, 190, 1874.
[52] Bahrami, K.; Khodaei, M. M.; Naali, F. J. Exp. Nanosci. 2016, 11, 148.
[53] Esmaeilpour, M.; Sardarian, A. R. Green Chem. Lett. Rev. 2014, 7, 301.
[54] Jafarpour, M.; Rezapour, E.; Ghahramaninezhad, M.; Rezaeifard, A. New J. Chem. 2014, 38, 676.
[55] Jafarpour, M.; Rezaeifard, A. Transition Met. Chem. 2015, 41, 205.
[56] Rajabi, F.; Alves, D.; Luque, R. Molecules 2015, 20, 20709.
[57] Javidi, J.; Esmaeilpour, M. Mater. Res. Bull. 2016, 73, 409.
[58] Edayadulla, N.; Lee, Y. R. RSC Adv. 2014, 4, 11459.
[59] Wang, Z.; Hu, G.; Liu, J.; Liu, W.; Zhang, H.; Wang, B. Chem. Commun. 2015, 51, 5069.
[60] Azarifar, A.; Nejat-Yami, R.; Azarifar, D. J. Iran Chem. Soc. 2012, 10, 297.
[61] Mouradzadegun, A.; Ma'mani, L.; Mahdavi, M.; Rashid, Z.; Shafiee, A.; Foroumadi, A.; Dianat, S. RSC Adv. 2015, 5, 83530.
[62] Swami, S.; Devi, N.; Agarwala, A.; Singh, V.; Shrivastava, R. Tetrahedron Lett. 2016, 57, 1346.
[63] Paul, S.; Pradhan, K.; Ghosh, S.; De, S. K.; Das, A. R. Tetrahedron 2014, 70, 6088.
[64] Santra, S.; Bagdi, A. K.; Majee, A.; Hajra, A. RSC Adv. 2013, 3, 24931.
[65] Farrokhi, A.; Ghodrati, K.; Yavari, I. Catal. Commun. 2015, 63, 41.
[66] Maleki, A.; Aghaei, M.; Ghamari, N. Chem. Lett. 2015, 44, 259.
[67] Zhang, J.; Ren, D. C.; Ma, Y. M.; Wang, W. T.; Wu, H. Tetrahedron 2014, 70, 5274.
[68] Zhang, J.; Zhao, J. W.; Wang, L. P.; Liu, J.; Ren, D. C.; Ma, Y. M. Tetrahedron 2016, 72, 936.
[69] Zhang, J.; Liu, J.; Ma, Y. M.; Ren, D. C.; Cheng, P.; Zhao, J. W.; Zhang, F.; Yao, Y. Bioorg. Med. Chem. Lett. 2016, 26, 2273.
[70] Zhang, J.; Cheng, P.; Ma, Y. M.; Liu, J.; Miao, Z.; Fan, C. Chin. J. Org. Chem. 2016, 36, 1368 (in Chinese).(张金, 程佩, 马养民, 刘佳, 苗智, 范超, 有机化学, 2016, 36, 1368.)
[71] Zhang, J.; Liu, J.; Ma, Y. M.; Yang, X. F.; Cheng, P.; Fan, C.; Lu, P. Chem. J. Chin. Univ. 2016, 37, 1629 (in Chinese).(张金, 刘佳, 马养民, 杨秀芳, 程佩, 范超, 卢萍, 高等学校化学学报, 2016, 37, 1629.)
/
| 〈 |
|
〉 |
