综述与进展

吡啶类含能化合物的合成研究进展

  • 马丛明 ,
  • 刘祖亮 ,
  • 许晓娟 ,
  • 姚其正
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  • a 南京理工大学化工学院 南京 210094;
    b 盐城师范学院化学化工学院 盐城 224002;
    c 中国药科大学药学院 南京 210009

收稿日期: 2014-02-25

  修回日期: 2014-03-14

  网络出版日期: 2014-04-02

基金资助

国家自然科学基金(No.21102125)资助项目.

Research Progress on the Synthesis of Energetic Pyridines

  • Ma Congming ,
  • Liu Zuliang ,
  • Xu Xiaojuan ,
  • Yao Qizheng
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  • a School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094;
    b Department of Chemistry, Yancheng Teachers University, Yancheng 224002;
    c School of Pharmacy, China Pharmaceutical University, Nanjing 210009

Received date: 2014-02-25

  Revised date: 2014-03-14

  Online published: 2014-04-02

Supported by

Project supported by the National Natural Science Foundation of China (No. 21102125).

摘要

吡啶类化合物在含能材料领域中的研究和应用较为广泛. 从分子结构出发,按照硝基吡啶、吡啶类含能离子盐和吡啶类含能配合物分类,综述了多种吡啶硝基衍生物的合成,并简单介绍了一些重要的硝基吡啶类含能化合物的特性及主要应用.

本文引用格式

马丛明 , 刘祖亮 , 许晓娟 , 姚其正 . 吡啶类含能化合物的合成研究进展[J]. 有机化学, 2014 , 34(7) : 1288 -1299 . DOI: 10.6023/cjoc201402030

Abstract

Pyridines are widely used in energetic materials. Based on molecular structure, and classified themselves by nitropyridines, pyridine-based energetic salts, pyridine-based energetic complexes, a large number of energetic pyridines are summarized. The characteristics and main applications of some important energetic pyridines are also introduced briefly.

参考文献

[1] Klapötke, T. M.; Penger, A.; Pflüger, C.; Stierstorfer, J.; Su?eska, M. Eur. J. Inorg. Chem. 2013, 2013, 4667.

[2] Zhang, Q.-H.; Zhang, J.-H.; Parrish, D. A.; Shreeve, J. M. Chem. Eur. J. 2013, 19, 11000.

[3] Fischer, D.; Klapötke, T. M.; Piercey, D. G.; Stierstorfer, J. Chem. Eur. J. 2013, 19, 4602.

[4] Dippold, A. A.; Izsak, D.; Klapötke, T. M. Chem. Eur. J. 2013, 19, 12042.

[5] Dippold, A. A.; Klapötke, T. M. J. Am. Chem. Soc. 2013, 135, 9931.

[6] Millar, R. W.; Philbin, S. P.; Claridge, R. P.; Hamid, J. Propellants, Explos., Pyrotech. 2004, 29, 81.

[7] Gao, H.-X.; Shreeve, J. M. Chem. Rev. 2011, 111, 7377.

[8] Jadhav, H. S.; Talawar, M. B.; Sivabalan, R.; Dhavale, D. D.; Asthana, S. N.; Krishnamurthy, V. N. J. Hazard. Mater. 2007, 143, 192.

[9] Duddu, R.; Dave, P. R.; Damavarapu, R.; Surapaneni, R.; Parrish, D. Synth. Commun. 2009, 39, 4282.

[10] Duddu, R.; Dave, P. R.; Damavarapu, R.; Gelber, N.; Parrish, D. Tetrahedron Lett. 2010, 51, 399.

[11] Singh, G.; Kapoor, I. P. S.; Mannan, S. M.; Tiwari, S. K. J. Hazard. Mater. 1999, 68, 155.

[12] Agrawal, J. P. Prop. Explos. Pyrotech. 2005, 30, 316.

[13] Lv, C.-X.; Li, G.-X. Explos. Mater. 1988, 137, 12 (in Chinese).

(吕春绪, 李广学, 爆破器材, 1988, (3), 12.)

[14] Zhang, J.-G.; Zhang, T.-L.; Zhang, Z.-G.; Yang, L. Chin. J. Energ. Mater. 2001, 9, 90 (in Chinese).

(张建国, 张同来, 张志刚, 杨利, 含能材料, 2001, 9, 90.)

[15] Boddu, V. M.; Viswanath, D. S.; Ghosh, T. K.; Damavarapu, R. J. Hazard. Mater. 2010, 181, 1.

[16] Carter, J. A.; Zaug, J. M.; Nelson, A. J.; Armstrong, M. R.; Manaa, M. R. J. Phys. Chem. A 2012, 116, 4851.

[17] Nandi, A. K.; Ghosh, M.; Sutar, V. B.; Pandey, R. K. Cent. Eur. J. Energ. Mater. 2012, 9, 119.

[18] Paraskos, A. J.; Kramer, M. P. US 7763753, 2010 [Chem. Abstr 2010, 153, 264293].

[19] Li, J.-S.; Huang, Y.-G.; Dong, H.-S.; Yang, G.-C. Chin. J. Energ. Mater. 2003, 11, 177 (in Chinese).

(李金山, 黄奕刚, 董海山, 杨光成, 含能材料, 2003, 11, 177.)

[20] Li, J.-S.; Huang, Y.-G.; Dong, H.-S. Chin. J. Energ. Mater. 2004, 12, 576.

(李金山, 黄奕刚, 董海山, 含能材料, 2004, 12, 576.)

[21] Li, J.-S.; Huang, Y.-G.; Dong, H.-S. J. Energ. Mater. 2005, 23, 133.

[22] Zhao, J.-M.; Li, J.-R.; Wei, X.-J.; Li, W.-T.; Dong, H.-S. Chin. J. Explos. Propellants 2006, 29, 73 (in Chinese).

(赵建民, 李加荣, 魏筱洁, 李文婷, 董海山, 火炸药学报, 2006, 29, 73.)

[23] Li, J.-R.; Zhao, J.-M.; Dong, H.-S. J. Chem. Crystallogr. 2005, 35, 943.

[24] He, Z.-W.; Gao, D.-Y.; Liu, Z.-L. Chin. J. Explos. Propellants 2009, 32, 32 (in Chinese).

(何志伟, 高大元, 刘祖亮, 火炸药学报, 2009, 32, 32.)

[25] Zhou, X.-L.; Liu, Z.-L.; Cheng, J.; Su, Q.; Hao, Y.-G.; Hu, B.-C. Chin. J. Energ. Mater. 2013, 21, 423 (in Chinese).

(周心龙, 刘祖亮, 成健, 苏强, 郝尧刚, 胡炳成, 含能材料, 2013, 21, 423.)

[26] Wang, B.-G.; Zhang, J.-L.; Chen, Y.-F. Chin. J. Energ. Mater. 2007, 15, 198 (in Chinese).

(王保国, 张景林, 陈亚芳, 含能材料, 2007, 15, 198.)

[27] Chang, H. Chin. J. Explos. Propellants 2007, 30, 36 (in Chinese).

(常海, 火炸药学报, 2007, 30, 36.)

[28] Wan, D.-Z. Chin. Sci. Bull. 1985, 1723 (in Chinese).

(万道正, 科学通报, 1985, 1723.)

[29] Licht, H. H.; Ritter, H. Prop. Explos. Pyrotech. 1988, 13, 25.

[30] Bannert, K.; Richter, S.; Schaarschmidt, D.; Lang, H. Angew. Chem., Int. Ed. 2013, 52, 3499.

[31] Huynh, M. V.; Hiskey, M. A.; Hartline, E. L.; Montoya, D. P.; Gilardi, R. Angew. Chem., Int. Ed. 2004, 43, 4924.

[32] Klapötke, T. M.; Piercey, D. G.; Stierstorfer, J. Chem. Eur. J. 2011, 17, 13068.

[33] Huynh, M. H.; Hiskey, M. A.; Chavez, D. E.; Naud, D. L.; Gilardi, R. D. J. Am. Chem. Soc. 2005, 127, 12537.

[34] Crawford, M. J.; Ellern, A.; Mayer P. Angew. Chem., Int. Ed. 2005, 44, 7874.

[35] Zhang, Q.-H.; Shreeve, J. M. Angew. Chem., Int. Ed. 2013, 52, 8792.

[36] Lowe-Ma, C. K.; Nissan, R. A.; Wilson, W. S. J. Org. Chem. 1990, 55, 3755.

[37] VanAllan, J. A.; Reynolds, G. A. J. Heterocycl. Chem. 1968, 5, 471.

[38] Carboni, R. A.; Castle, J. E. J. Am. Chem. Soc. 1962, 84, 2453.

[39] Kauer, J. C.; Carboni, R. A. J. Am. Chem. Soc. 1967, 89, 2633.

[40] Balachari, D.; Trudell, M. L. Tetrahedron Lett. 1997, 38, 8607.

[41] Balachari, D.; Stevens, E. D.; Trudell, M. L.; Beardall, D.; Wight, C. A. Propellants, Explos., Pyrotech. 2000, 25, 75.

[42] Albini, A.; Pietra, S. Heterocyclic N-Oxide, CRC Press, Boca Raton, Florida, 1991.

[43] Ritter, H.; Licht, H. H. J. Heterocycl. Chem. 1995, 32, 585.

[44] Cheng, J.; Yao, Q.-Z.; Zhou, X.-L.; Du, Y.; Fang, D.; Liu, Z.-L. Chin. J. Energ. Mater. 2008, 16, 672 (in Chinese).

(成健, 姚其正, 周新利, 杜杨, 方东, 刘祖亮, 含能材料, 2008, 16, 672.)

[45] Cheng, J.; Yao, Q.-Z.; Zhou, X.-L.; Du, Y.; Fang, D.; Liu, Z.-L. Chin. J. Org. Chem. 2008, 28, 1943 (in Chinese).

(成健, 姚其正, 周新利, 杜杨, 方东, 刘祖亮, 有机化学, 2008, 28, 1943.

[46] Cheng, J.; Yao, Q.-Z.; Dong, Y.; Liu, Z.-L. Chin. J. Energ. Mater. 2009, 17, 534 (in Chinese).

(成健, 姚其正, 董岩, 刘祖亮, 含能材料, 2009, 17, 534.)

[47] Wang, Y.-H.; Song, Y.-J.; Hu, Z.; Jing, J.-H.; Meng, X.-L.; Huang, Y.-D. Chin. J. Org. Chem. 2009, 29, 780 (in Chinese).

(王艳红, 宋元军, 胡桢, 景介辉, 孟祥丽, 黄玉东, 有机化学, 2009, 29, 780.)

[48] Ma, C.-M.; Hou, K.-H.; Liu, Z.-L.; Yao, Q.-Z. Chin. J. Org. Chem. 2014, 34, 584 (in Chinese).

(马丛明, 侯可辉, 刘祖亮, 姚其正, 有机化学, 2014, 34, 584.)

[49] Licht, H. H. Propellants, Explos., Pyrotech. 2002, 25, 126.

[50] He, Z.-W.; Cheng, J.; Liu, Z.-L. Chin. J. Energ. Mater. 2009, 17, 392 (in Chinese).

(何志伟, 成健, 刘祖亮, 含能材料, 2009, 17, 392.)

[51] He, Z.-W.; Liu, Z.-L.; Wang, A.-L. Chin. J. Explos. Propellants 2010, 22, 11 (in Chinese).

(何志伟, 刘祖亮, 王爱玲, 火炸药学报, 2010, 22(1), 11.)

[52] An, C.-W.; Song, X.-L.; Wang, Y.; Guo, X.-D.; Li, F.-S. Chinese J. Energ. Mater. 2007, 15, 188 (in Chinese).

(安崇伟, 宋小兰, 王毅, 郭效德, 李凤生, 含能材料, 2007, 15, 188.)

[53] Chen, L.-Y.; Zhao, S.-X.; Yang, P.-J.; Heng, S.-Y.; Li, W.; Huang, X.-W. Chin. J. Energ. Mater. 2006, 14, 171 (in Chinese).

(陈鲁英, 赵省向, 杨培进, 衡淑云, 李巍, 黄小梧, 含能材料, 2006, 14, 171.)

[54] He, Z.-W.; Gao, D.-Y.; Fang, D.; Liu, Z.-L. Chin. J. Energ. Mater. 2009, 17, 299 (in Chinese).

(何志伟, 高大元, 方东, 刘祖亮, 含能材料, 2009, 17, 299.)

[55] He, Z.-W.; Liu, Z.-L. Chin. J. Explos. Propellants 2013, 36, 21 (in Chinese).

(何志伟, 刘祖亮, 火炸药学报, 2013, 36, 21.)

[56] He, Z.-W.; Liu, Z.-L. Chin. J. Energ. Mater. 2010, 18, 97 (in Chinese).

(何志伟, 刘祖亮, 含能材料, 2010, 18, 97.)

[57] Durante, V. A.; Karmakar, S. US 5861536, 1999 [Chem. Abstr. 1999, 130, 111835].

[58] Bakke, J. M.; Harald, S. Tetrahedron Lett. 2001, 42, 4393.

[59] Cheng, J.; Liu, Z.-L.; Yao, Q.-Z.; Zhou, X.-L.; Wang, A.-L. Chin. J. Explos. Propellants 2009, 32, 5 (in Chinese).

(成健, 刘祖亮, 姚其正, 周新利, 王爱玲, 火炸药学报, 2009, 32, 5.)

[60] Cheng, J.; Zhou, X.-L.; Qiao, Z.; Yao, Q.-Z.; Liu, Z.-L. Chin. J. Energ. Mater. 2009, 17, 296 (in Chinese).

(成健, 周新利, 乔珍, 姚其正, 刘祖亮, 含能材料, 2009, 17, 296.)

[61] Wo?niak, M.; Bańskira, A.; Szpakiewicz, B. Liebigs Ann. Chem. 1993, 1, 7.

[62] de Bie, D. A.; Geurtsen, B.; van der Plas, H. C. J. Org. Chem. 1985, 50, 484.

[63] Hollins, R. A.; Merwin, L. M.; Nissan, R. A. J. Heterocycl. Chem. 1996, 33, 895.

[64] Badgujar, D. M.; Talawar, M. B.; Asthana, S. N.; Mahulikar, P. P. J. Hazard. Mater. 2008, 151, 289.

[65] Ritter, H.; Licht, H. H. Propellants, Explos., Pyrotech. 1993, 18, 81.

[66] Ma, C.-M.; Wang, Y.-B.; Hou K.-H.; Liu, Z.-L.; Yao, Q.-Z. Chin. J. Chem. 2013, 31, 1299.

[67] Mitchell, A. R.; Pagoria, P. F.; Coon, C. L.; Jessop, E. S.; Poco, J. F.; Tarver, C. M. Breithaupt, R. D.; Moody, G. L. Propellants, Explos., Pyrotech. 1994, 19, 232.

[68] Zhou, C.; Zhou, Y.-S.; Huo, H,; Wang B.-Z.; Zhang, Y.-G. Chin. J. Explos. Propellants 2011, 34, 17 (in Chinese).

(周诚, 周彦水, 霍欢, 王伯周, 张叶高, 火炸药学报, 2011, 34, 17.)

[69] Peng, Z.-J.; Wan, D.-Z. Acta Armament 1980, 3, 23 (in Chinese).

(彭忠吉, 万道正, 兵工学报, 1980, 3, 23.)

[70] Boileau, J.; Emeury, J. L.; Kehren, J. US 4487938, 1984 [Chem. Abstr. 1985, 102, 169227].

[71] Chaykovsky, M.; Adolph, H. G. J. Heterocycl. Chem. 1991, 28, 1491.

[72] Coburn, M. D. US 3678061, 1972 [Chem. Abstr. 1972, 77, 139812].

[73] Riggs, R. S. US 4948897, 1990 [Chem. Abstr. 1990, 112, 9513].

[74] Wang, N.-X. Chin. J. Explos. Propellants 1993, (4), 21 (in Chinese).

(王乃兴, 火炸药, 1993, (4), 21.)

[75] Wang, N.-X.; Chen, B.-R.; Ou, Y.-X. Chin. J. Explos. Propellants 1992, (4), 6 (in Chinese).

(王乃兴, 陈博仁, 欧育湘, 火炸药, 1992, (4), 6.)

[76] Wang, N.-X. Chin. J. Energ. Mater. 1995, 3, 44 (in Chinese).

(王乃兴, 含能材料, 1995, 3, 44.)

[77] Wang, N.-X.; Chen, B.R.; Qu, Y.-X. Chem. World 1993, 34, 254.

(王乃兴, 陈博仁, 欧育湘, 化学世界, 1993, 34, 254.)

[78] Wang, N.-X.; Li, J.-S. Chin. J. Energ. Mater. 1994, 2, 25 (in Chinese).

(王乃兴, 李纪生, 含能材料, 1994, 2, 25.)

[79] Wang, N.-X.; Chen, B.-R.; Ou, Y.-X. J. Beijing Inst. Technol. 1994, 14, 33 (in Chinese).

(王乃兴, 陈博仁, 欧育湘, 北京理工大学学报, 1994, 14, 33.)

[80] Coburn, M. D.; Singleton, J. L. J. Heterocycl. Chem. 1972, 9, 1039.

[81] Jadhav, H. S.; Talwar, M. B.; Dhavale, D. D.; Asthana, S. N.; Krishnamurthy, V. N. Ind. J. Heterocycl. Chem. 2006, 15, 383.

[82] Singh, R. P.; Verma, R. D.; Meshri, D. T.; Shreeve, J. M. Angew. Chem., Int. Ed. 2006, 45, 3584.

[83] Hong, X.; Arritt, S. W.; Twamley, B.; Shreeve, J. M. Inorg. Chem. 2004, 43, 7972.

[84] Galves-Ruiz, J. C.; Holl, G. H.; Karaghiosoff, K.; Klapötke, T. M.; Löhnwitz, K.; Mayer, P.; Nöth, H.; Polborn, K.; Rohbogner, C. J.; Suter, M.; Weigand, J. J. Inorg. Chem. 2005, 44, 4237.

[85] Thottempudi, V.; Yin, P.; Zhang, J.-H.; Parrish, D. A.; Shreeve, J. M. Chem. Eur. J. 2014, 20, 542.

[86] Klapötke, T. M.; Piercey, D. G.; Stierstorfer, J. Eur. J. Inorg. Chem. 2013, 2013, 1509.

[87] Song, J.-H.; Wang, K.; Liang, L.-X.; Bian, C.-M.; Zhou, Z.-M. RSC Adv. 2013, 3, 10859.

[88] Liang, L.-X.; Cao, D.; Song, J.-H.; Huang, H.-F.; Wang, K.; Bian, C.-M.; Dong, X.; Zhou, Z.-M. J. Mater. Chem. A 2013, 1, 8857.

[89] Gao, H.-X.; Ye, C.-F.; Gupta, O. D.; Xiao, J.; Hiskey, M. A.; Twamley, B.; Shreeve, J. M. Chem. Eur. J. 2007, 13, 3853.

[90] Huang, Y.-G.; Gao, H.-X.; Twamley, B.; Shreeve, J. M. Eur. J. Inorg. Chem. 2007, 2025.

[91] Wang, Y.-L.; Zhao, F.-Q.; Xu, K.-Z.; Ji, Y.-P.; Yi, J.-H.; Chen, B.; An, T. Inorg. Chim. Acta 2013, 405, 505.

[92] Klapötke, T. M.; Mayer, P.; Sabate, C. M.; Welch, J. M.; Wiegand, N. Inorg. Chem. 2008, 47, 6014.

[93] Zhang, G.-F.; She, J. B.; Dou, Y.-L.; Fan, R. Z. Kristallogr.-New Cryst. Struct. 2006, 221, 183.

[94] Tang, F.-Y.; She, J. B.; Zhang, G.-F. Z. Kristallogr.-New Cryst. Struct. 2006, 221, 539.

[95] Zheng, Y.-M.; Deng, M.-Z.; Zhao, F.-Q.; Yuan, C. Chin. J. Explos. Propellants 2002, 25, 51 (in Chinese).

(郑玉梅, 邓敏智, 赵凤起, 袁潮, 火炸药学报, 2002, 25, 51.)

[96] Chen, P.; Zhao, F.-Q.; Luo, Y.; Hu, R.-Z.; Zheng, Y.-M.; Deng, M.-Z.; Gao, Y. Acta Chim. Sinica 2004, 62, 1197 (in Chinese).

(陈沛, 赵凤起, 罗阳, 胡荣祖, 郑玉梅, 邓敏智, 高茵, 化学学报, 2004, 62, 1197.)

[97] Zhao, F.-Q.; Chen, P.; Luo, Y.; Zhang, R.-E.; Li, S.-W.; Deng, M.-Z.; Zheng, Y.-M. Chin. J. Explos. Propellants 2003, 26, 1 (in Chinese).

(赵凤起, 陈沛, 罗阳, 张蕊娥, 李上文, 邓敏智, 郑玉梅, 火炸药学报, 2003, 26, 1.)

[98] Zhang, G.-F.; She, J.-B.; Li, D.-D.; Li, J.-Z.; Zhou, Q.-P.; Dou, Y.-L.; Fan, X.-Z.; Hu, M.-C.; Liu, Z.-H. J. Coord. Chem. 2008, 61, 865.

[99] Zhou, Q.-P.; Zhang, G.-F.; She, J.-B. J. Coord. Chem. 2008, 61, 2601.

[100] She, J.-B.; Zhang, G.-F.; Zhao, F.-Q.; Lei, Z.-L.; Fan, X.-Z. Struct. Chem. 2007, 18, 373.

[101] Zhang, G.-F.; Yasen·Musa, Zhao, F.-Q.; Fan, X.-Z. Chin. J. Energ. Mater. 2012, 20, 126 (in Chinese).

(张国防, 亚森·木萨, 赵凤起, 樊学忠, 含能材料, 2012, 20, 126.)

[102] Cai, M.-Y.; Zhang, G.-F.; Zhou, H.-B.; Jing, P.; He, C. J. Shaanxi Normal Univ. (Nat. Sci. Ed.) 2010, (3), 43 (in Chinese).

(蔡美玉, 张国防, 周海波, 景萍, 何冲, 陕西师范大学学报(自然科学版), 2010, (3), 43.)

[103] Ghule, V. D.; Srinivas, D.; Muralidharan, K. Asian J. Org. Chem. 2013, 2, 662.

[104] Zhang, J.-G.; Zhang, T.-L.; Zhang, Z.-G.; Yang, L. Chin. J. Energ. Mater. 2001, 9, 90 (in Chinese).

(张建国, 张同来, 张志刚, 杨利, 含能材料, 2001, 9, 90.)

[105] Liu, J.-J.; Liu, Z.-L.; Lin, X.-Y.; Cheng, J.; Fang, D. Chin. J. Energ. Mater. 2013, 21, 644 (in Chinese).

(刘进剑, 刘祖亮, 蔺向阳, 成健, 方东, 含能材料, 2013, 21, 644.)

[106] Liu, J.-J.; Liu, Z.-L.; Cheng, J.; Fang, D. Chin. J. Energ. Mater. 2013, 21, 711 (in Chinese).

(刘进剑, 刘祖亮, 成健, 方东, 含能材料, 2013, 21, 711.)

[107] Liu, J.-J.; Liu, Z.-L.; Lin, X.-Y.; Cheng, J.; Fang, D. J. Nanjing Univ. Sci. Technol. 2013, 37, 640 (in Chinese).

(刘进剑, 刘祖亮, 蔺向阳, 成健, 方东, 南京理工大学学报, 2013, 37, 640.)

[108] Liu, J.-J.; Liu, Z.-L.; Cheng, J.; Fang, D. RSC Adv. 2013, 3, 2917.

[109] Liu, J.-J.; Liu, Z.-L.; Cheng, J. Chin. J. Explos. Propellants 2012, 35, 36 (in Chinese).

(刘进剑, 刘祖亮, 成健, 火炸药学报, 2012, 35, 36.)

[110] Liu, J.-J.; Liu, Z.-L.; Cheng, J. J. Solid State Chem. 2013, 197, 198.

[111] Liu, J.-J.; Liu, Z.-L.; Cheng, J.; Fang, D. J. Solid State Chem. 2013, 200, 43.

[112] Liu, J.-J.; Liu, Z.-L.; Cheng, J.; Fang, D.; Wang, J. Chin. J. Inorg. Chem. 2013, 29, 289.

(刘进剑, 刘祖亮, 成健, 方东, 王俊, 无机化学学报, 2013, 29, 289.)

[113] Yamanouchi, K.; Enemark, J. H. Inorg. Chem. 1978, 17, 2911.

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