1,4-二氢吡啶的合成研究进展

doi:10.6023/cjoc201604050

摘要/Abstract

1，4-二氢吡啶（1，4-DHPs）是具有广泛生理活性和应用价值的重要氮杂环化合物.随着绿色有机合成化学的发展，1，4-DHPs的绿色合成和新合成方法在近些年取得了一些重要研究成果，弥补了Hantzsch反应的传统合成途径的一些不足，如环境友好、合成效率、产物结构单一和反应类型匮乏等.对2010年以来Hantzsch反应的绿色合成和新合成方法进行综述，全面地介绍了Hantzsch反应中绿色溶剂、绿色催化剂和绿色合成技术的应用，以及基于新砌块发展出合成1，4-DHPs的新反应研究现状，系统地分析了Hantzsch反应的绿色合成及新型反应的合成策略特点，详细地阐述反应底物、反应条件和产率，进而从新反应的绿色合成化和手性合成等方面对该领域的研究方向进行了探讨.

关键词: 1,4-二氢吡啶, Hantzsch反应, 清洁合成, 烯胺酮

1,4-Dihydropyridines (1,4-DHPs) are an important class of heterocyclic compounds, and possess a broad array of biological activities and applications. With the development of green organic synthetic chemistry, some important achievements have been made in the green synthesis of 1,4-DHPs and new synthetic methods, which made up some shortcomings of the traditional synthesis of Hantzch reaction, such as environment friendly, synthesis efficiency, single product structure and lack of reaction type. This review provides the first overview for the green synthesis of Hantzch reaction and new synthetic methods of 1,4-DHPs since 2010. A comprehensive and up-to-date introduction are given for Hantzch reaction under geen solvent, geen catalyst and geen synthetic technology, and the new reaction of synthesis of 1,4-DHPs based on new building blocks. A thorough analysis is provided concerning the feature of improvement of green synthesis of Hantzsch reaction and new synthetic method. Moreover, the substrates, conditions, selectivities and yields have been also described. Finally, a brief discussion relating to developments and potential areas of further research concerning new synthetic methods of 1,4-DHPs and green synthesis, and chiral synthesis, is presented.

Key words: 1,4-dihydropyridines, Hantzsch reaction, clean synthesis, enaminone

引用此文

鲁玲玲, 许辉, 周攀, 余富朝. 1,4-二氢吡啶的合成研究进展[J]. 有机化学, 2016, 36(12): 2858-2879.

Lu Lingling, Xu Hui, Zhou Pan, Yu Fuchao. Progress in Synthesis of 1,4-Dihydropyridines[J]. Chinese Journal of Organic Chemistry, 2016, 36(12): 2858-2879.

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参考文献

[1] (a) Rovnyak, G. C.; Kimball, S. D.; Beyer, B.; Cucinotta, G.; Dimarco, J. D.; Gougoutas, J.; Hedberg, A.; Malley, M.; MaCarthy, J. P.; Zhang, R.; Mereland, S. J. Med. Chem. 1995, 38, 119.
(b) Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803.
(c) Hilgeroth, A. Mini-Rev. Med. Chem. 2002, 2, 235.
(d) Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1403.
(e) Natale, N. R.; Rogers, M. E.; Staples, R.; Triggle, D. J.; Rutledge, A. J. Med. Chem. 1999, 42, 3087.
[2] (a) Chu, C. K.; Bhadti, V. S.; Doshi, K. J.; Etse, J. T.; Gallo, J. M.; Boudinot, F. D.; Schinazi, R. F. J. Med. Chem. 1990, 33, 2188.
(b) Hilgeroth, A.; Lilie, H. Eur. J. Med. Chem. 2003, 38, 495.
[3] Refat, H. M.; Fadda, A. A. Eur. J. Med. Chem. 2013, 70, 419.
[4] (a) Surendra Kumar, R.; Idhayadhulla, A.; Jamal Abdul Nasser, A.; Kavimani, S.; Indumathy, S. Indian J. Pharm. Sci. 2010, 72, 719.
(b) Subudhi, B. B.; Panda, P. K.; Swain, S. P.; Sarangi, P. Acta Pol. Pharm. 2009, 66, 147.
[5] (a) Abbas, H. A.; El Sayed, W. A.; Fathy, N. M. Eur. J. Med. Chem. 2010, 45, 973.
(b) Morshed, S. R.; Hashimoto, K.; Murotani, Y.; Kawase, M.; Shah, A.; Satoh, K.; Kikuchi, H.; Nishikawa, H.; Maki, J.; Sakagami, H. Anticancer Res. 2005, 25, 2033.
(c) Robert, J.; Jarry, C. J. Med. Chem. 2003, 46, 4805.
[6] Klusa, V. Drugs Future 1995, 20, 135.
[7] Donkor, I. O.; Zhou, X.; Schmidt, J.; Agrawal, K. C.; Kishore, V. Bioorg. Med. Chem. 1998, 6, 563.
[8] (a) Straub, T.; Boesenberg, C.; Gekeler, V.; Boege, F. Biochemistry 1997, 36, 10777.
(b) Briede, J.; Stivrina, M.; Vigante, B.; Stoldere, D.; Duburs, G. Cell Biochem. Funct. 2008, 26, 238.
(c) Schade, D.; Lanier, M.; Willems, E.; Okolotowicz, K.; Bushway, P.; Wahlquist, C.; Gilly, G.; Mercola, M.; Cashman, J. R. J. Med. Chem. 2012, 55, 9946.
[9] (a) Mao, Y. Z.; Jin, M. Z.; Liu, Z. L.; Wu, L.-M. Org. Lett. 2000, 2, 741.
(b) Zhang, D.; Wu, L.-Z.; Zhou, L.; Han, X.; Yang, Q.-Z.; Zhang, L.-P.; Tung, C.-H. J. Am. Chem. Soc. 2004, 126, 3440.
(c) Fang, X.-Q.; Liu, Y.-C.; Li, C.-Z. J. Org. Chem. 2007, 72, 8608.
(d) Jiang, J.; Yu, J.; Sun, X.-X.; Rao, Q.-Q.; Gong, L.-Z. Angew. Chem., Int. Ed. 2008, 47, 2458.
[10] (a) Menche, D.; Hassfeld, J.; Li, J.; Menche, G.; Ritter, A.; Rudolph, S. Org. Lett. 2006, 8, 741.
(b) Li, G.; Antilla, J. C. Org. Lett. 2009, 11, 1075.
(c) Itoht, T.; Anagata, K.; Miyazaki, M.; Ishikawa, H.; Kurihara, A.; Ohsawa, A. Tetrahedron 2004, 60, 6649.
(d) Rueping, M.; Theissmann, T.; Raja, S.; Batsa, J. W. Adv. Synth. Catal. 2008, 350, 1001.
(e) Hoffmann, S.; Nicoletti, M.; List, B. J. Am. Chem. Soc. 2006, 128, 13074.
(f) Rueping, M.; Dufour, J.; Schoepke. F. R. Green Chem. 2011, 13, 1084.
(g) Richter, D.; Mayr, H. Angew. Chem., Int. Ed. 2009, 48, 1958.
[11] (a) Hantzsch, A. Chem. Ber. 1881, 14, 1637.
(b) Wu, P.; Xia, E.-Y.; Sun, J.; Yan, C.-G. Chem. Res. Chin. Univ. 2012, 28, 652.
[12] (a) Yadav, D. K.; Patel, R.; Srivastava, V. P.; Watal, G.; Yadav, L. D. S. Chin. J. Chem. 2011, 29, 118.
(b) Li, J-P.; Qiu, J.-K.; Li, H.-J.; Zhang, G.-S. Chin. J. Chem. 2011, 29, 511.
(c) Baraldi, P. T.; Noël, T.; Wang, Q.; Hessel, V. Tetrahedron Lett. 2014, 55, 2090.
[13] Wang, D.-L.; Lin, L.-N.; Li, S.-F.; Li, W.; Li, Y.-F. Chin. J. Org. Chem. 2010, 30, 1774(in Chinese).(王道林, 林力男, 李少飞, 李伟, 李元峰. 有机化学, 2010, 30, 1774.)
[14] (a) Gati, W.; Rammah, M. M.; Rammah, M. B.; Couty, F.; Evano, G. J. Am. Chem. Soc. 2012, 134, 9078.
(b) Fructos, M. R.; Álvarez, E.; Díaz-Requejo, M. M.; Pérez, P. J. J. Am. Chem. Soc. 2010, 132, 4600.
(c) Girling, P. R.; Batsanov, A. S.; Shenb, H. C.; Whiting, A. Chem. Commun. 2012, 48, 4893.
(d) Nakaike, Y.; Nishiwaki, N.; Ariga, M.; Tobe, Y. J. Org. Chem. 2014, 79, 2163.
[15] (a) Liu, L.; Sarkisian, R.; Deng, Y.; Wang, H. J. Org. Chem. 2013, 78, 5751.
(b) Shao, Y.; Zhu, K.; Qin, Z.; Li, E.; Li, Y. J. Org. Chem. 2013, 78, 5731.
(c) Harschneck, T.; Kirsch, S. F. J. Org. Chem. 2011, 76, 2145.
(d) Wen, L.-R.; Shi, Y.-J.; Liu, G.-Y.; Li, M. J. Org. Chem. 2012, 77, 4252.
(e) Noole, A.; Borissova, M.; Lopp, M.; Kanger, T. J. Org. Chem. 2011, 76, 1538.
(f) Sun, J.; Xia, E.-Y.; Wu, Q.; Yan, C.-G. Org. Lett. 2010, 12, 3678.
(g) Asahara, H.; Hamada, M.; Nakaike, Y.; Nishiwaki, N. RSC Adv. 2015, 5, 90778.
[16] (a) Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563.
(b) Yeung, D. K. J.; Gao, T.; Huang, J.; Sun, S.; Guo, H.; Wang, J. Green Chem. 2013, 15, 2384.
[17] Zonouz, A. M.; Sahranavard, N. Eur.-J. Chem. 2010, 7, S372.
[18] Tamaddon, F.; Razmi, Z.; Jafari, A. A. Tetrahedron Lett. 2010, 51, 1187.
[19] Ghosh, P. P.; Mukherjee, P.; Das, A. R. RSC Adv. 2013, 3, 8220.
[20] Yang, J.-M.; Jiang, C.-N.; Yang, J.-J.; Qian, C.-W.; Fang, D. Green Chem. Lett. Rev. 2013, 6, 262.
[21] Khaskel, A.; Barman, P.; Jana, U. RSC Adv. 2015, 5, 13366.
[22] Niaz, H.; Kashtoh, H.; Khan, J. A.J.; Khan, A.; Wahab, A.; Alam, M. T.; Khan, K. M.; Perveen, S.; Choudhary, M. I. Eur. J. Med. Chem. 2015, 95, 199.
[23] Tamaddon, F.; Ghazi, S. Catal. Commun. 2015, 72, 63.
[24] Sohal, H. S.; Khare, R.; Goyal, A.; Woolley, A.; Singh, K.; Sharma, R. Am. J. Chem. 2014, 4, 29.
[25] (a) Wolfson, A.; Dlugy, C.; Shotland, Y. Environ. Chem. Lett. 2007, 5, 67.
(b) Razler, T. M.; Hsiao, Y.; Qian, F.; Fu, R.; Khan, R. K.; Doubleday, W. J. Org. Chem. 2009, 74, 1831.
(c) Ghorbani-Choghamarani, A.; Moradi, P.; Tahmasbi, B. RSC Adv. 2016, 6, 43205.
[26] (a) Gu, Y.; Barrault, J.; Jerome, F. Adv. Synth. Catal. 2008, 350, 2007.
(b) Feu, K. S.; de la Torre, A. F.; Silva, S.; de Moraes Junior, M. A. F.; Corrêa, A. G.; Paixão, M. W. Green Chem. 2014, 16, 3169.
[27] (a) Karam, A.; Villandier, N.; Delample, M.; Koerkamp, C. K.; Douliez, J. P.; Granet, R.; Krausz, P.; Barrault J.; Jerome, F. Eur. J. Chem. 2008, 14, 10196.
(b) He, F., Li, P., Gu, Y., Li, G., Green Chem., 2009, 11, 1767.
[28] Radadiya, A.; Khedkar, V.; Bavishi, A.; Vala, H.; Thakrar, S.; Bhavsar, D.; Shah, A.; Coutinho, E. Eur. J. Med. Chem. 2014, 74, 375.
[29] (a) e Silva, F. A.; Caban, M.; Stepnowski, P.; Coutinhoa, J. A. P.; Ventura, S. P. M. Green Chem. 2016, 18, 3749.
(b) Kuwabata, S.; Tsuda, T.; Torimoto, T. J. Phys. Chem. Lett. 2010, 1, 3177.
(c) Horikoshi, S.; Hamamura, T.; Kajitani, M.; Yoshizawa-Fujita, M.; Serpone, N. Org. Process Res. Dev. 2008, 12, 1089.
[30] Reddy, B. P.; Rajesh, K.; Vijayakumar, V. J. Chin. Chem. Soc. 2011, 58, 384.
[31] Reddy, B. P.; Rajesh, K.; Vijayakumar, V. Arabian J. Chem. 2015, 8, 138.
[32] Safari, J.; Zarnegar, Z. RSC Adv. 2013, 3, 26094.
[33] Sharma, P.; Gupta, M. Green Chem. 2015, 17, 1100.
[34] Priede, E.; Zicmanis, A. Helv. Chim. Acta 2015, 98, 1095.
[35] Sheldon, R. A. J. Mol. Catal. 1996, 107, 75.
[36] Yu, F.-C.; Yan, S.-J.; Lin, J. Chin, J. Org. Chem. 2010, 30, 1421(in Chinese).(余富朝, 严胜骄, 林军. 有机化学, 2010, 30, 1421.)
[37] Mansoor, S. S.; Aswin, K.; Logaiya, K.; Sudhan, S. P. N. J. King Saud Univ., Sci. 2013, 25, 191.
[38] Liu, Y.-P.; Liu, J.-M.; Wang, X.; Cheng, T.-M.; Li, R.-T. Tetrahedron 2013, 69, 5242.
[39] Keyhani, A.; Hatamjafari, F. Orient. J. Chem. 2013, 29, 783.
[40] Murthy, Y. L. N.; Rajack, A.; Ramji, M. T.; Jeson babu, J.; Praveen, C.; Lakshmi, K. A. Bioorg. Med. Chem. Lett. 2012, 22, 6016.
[41] Kiasat, A.; Nazari, S.; Davarpanah, J. J. Serb. Chem. Soc. 2014, 79, 401.
[42] Nasr-Esfahani, M.; Montazerozohori, M.; Raeatikia, R. Maejo Int. J. Sci. Technol. 2014, 8, 32.
[43] Ramchander, J.; Raju, G.; Rameshwar, N.; Reddy, T. S.; Reddy, A. R. Spectrochim. Acta A:Mol. Biomol. Spectrosc. 2012, 85, 210.
[44] Rao, C. V. N.; Ramprasad, S.; Rao, P. V.; Subhani, S.; Gopi, Y. J. Chem. Pharm. Res. 2012, 4, 2112.
[45] Safari, J.; Azizi, F.; Sadeghi, M. New J. Chem. 2015, 39, 1905.
[46] (a) Carson, L; Kelly-Brown, C.; Stewart, M.; Oki, A.; Regisford, G.; Luo, Z.; Bakhmutov, V. I. Mater. Lett. 2009, 63, 617.
(b) CastrejLn-Parga, K. Y.; Camacho-Montes, H.; Rodrízguez-Gonzàlez, C. A.; Velasco-Santos, C.; Martínez-Hernàndez, A. L.; Bueno-Jaquez, D.; Rivera-Armenta, J. L.; Ambrosio, C. R.; Conzalez, C. C.; Mendoza-Duarte, M. E.; García-Casillas, P. E. J. Alloys Compd. 2013, 12, 269.
[47] (a) Lakshmikantam, M.; Mahendar, K.; Bhargava, S. J. Chem. Sci. 2010, 122, 63.
(b) Murugan, R.; Ramamoorthy, K.; Sundarrajan, S.; Ramakrishna, S. Tetrahedron 2012, 68, 7196.
(c) Mirzaei, H.; Davoodnia, A. Chin. J. Catal. 2012, 33, 1502.
[48] Pramanik, M.; Bhaumik, A. J. Mater. Chem. A 2013, 1, 11210.
[49] Koukabi, N.; Kolvari, E.; Khazaei, A.; Zolfigol, M. A.; Shirmardi-Shaghasemi, B.; Khavasi, H. R. Chem. Commun. 2011, 47, 9230.
[50] Maleki, A.; Kamalzare, M.; Aghaei, M. J. Nanostruct. Chem. 2015, 5, 95.
[51] Dam, B.; Nandi, S.; Pal, A. K. Tetrahedron Lett. 2014, 55, 5236.
[52] Zarnegar, Z.; Safari, J. Int. J. Biol. Macromol. 2015, 75, 21.
[53] Teimouri, A.; Ghorbanian, L.; Moatari, A. Bull. Chem. Soc. Ethiop. 2013, 27, 427.
[54] Tamaddon, F.; Moradi, S. J. Mol. Catal. A:Chem. 2013, 370, 117.
[55] Safaei-Ghomi, J.; Ziarati, A.; Teymuri, R. Bull. Korean Chem. Soc. 2012, 33, 2679.
[56] Viswanath, I. V. K.; Murthy, Y. L. N. Chem. Sci. Trans. 2013, 2, 227.
[57] Bitaraf, M.; Amoozadeh, A.; Otokesh, S. J. Chin. Chem. Soc. 2016, 64, 336.
[58] Kar, P.; Mishra, B. G. Chem. Eng. J. 2013, 223, 647.
[59] Teimouri, A.; Ghorbanian, L.; Moatari, A. Bull. Chem. Soc. Ethiop. 2013, 27, 427.
[60] Pei, W.; Li, F.-J.; Wang, H.-B.; Hu, N.-X.; Sun, L.; Li, X.-N. Chin. J. Org. Chem. 2011, 31, 1188(in Chinese).(裴文, 李风军, 王海滨, 胡香凝, 孙莉, 李小年. 有机化学, 2011, 31, 1188.)
[61] Dasgupta, S; Torok, B. Curr. Org. Synth. 2008, 5, 321.
[62] Pei, W.; Wang, Q.; Li, X.-N.; Sun, L. Chin. J. Chem. 2010, 28, 483.
[63] Datta, B.; M.Pasha, A. Chin. J. Catal. 2011, 32, 1180.
[64] Safaei-Ghomi, J.; Ziarati, A.; Zahedi, S. J. Chem. Sci. 2012, 124, 933.
[65] (a) Devassy, B. M.; Halligudi, S. B. J. Catal. 2005, 236, 313.
(b) Heydari, A.; Khaksar, S.; Sheykhan, M.; Tajbakhsh, M. J. Mol. Catal., A 2008, 287, 5.
[66] Ghattali, S. N.; Saidi, K.; Khabazzadeh, H. Res. Chem. Intermed. 2014, 40, 281.
[67] Tavakoli-Hoseini, N. J. Chil. Chem. Soc. 2012, 57, 1432.
[68] (a) Boey, P. L.; Ganesan, S.; Maniam, G. P.; Khairuddean M.; Lee, S. E. Appl. Catal. A:Gen. 2012, 12, 433.
(b) Dekamin, M. G.; Azimoshan, M.; Ramezani, L. Green Chem. 2013, 15, 811.
[69] Dekamin, M. G.; Ilkhanizadeh, S.; Latifidoost, Z.; Daemi, H.; Karimi, Z.; Barikani, M. RSC Adv. 2014, 4, 56658.
[70] Khan, A. T.; Lal, M.; Khan, M. M. Tetrahedron Lett. 2010, 51, 4419.
[71] Khaskel, A.; Barman, P. Heteroat. Chem. 2016, 27, 114.
[72] Ghosh, S.; Saikh, F.; Das, J.; Pramanik, A. K. Tetrahedron Lett. 2013, 54, 58.
[73] (a) Bogdal, D.; Loupy, A. Org. Process Res. Dev. 2008, 12, 710.
(b) Kempe, K.; Becer, C. R.; Schubert, U. S. Macromolecules 2011, 44, 5825.
[74] (a) Mithlesh; Pareek, P. K.; Kant, R.; Shukla, S. K.; Ojha, K. G. Cent. Eur. J. Chem. 2010, 8, 163.
(b) Mithlesh; Pareek, P. K.; Ravikant; Ojha, K. G. Pharm. Chem. 2011, 3, 66.
[75] Ladani, N. K.; Mungra, D. C.; Patel, M. E.; Patel, R. G. Chin. Chem. Lett. 2011, 22, 1407.
[76] Kuraitheerthakumaran, A.; Pazhamalai, S.; Gopalakrishnan, M. Chin. Chem. Lett. 2011, 22, 1199.
[77] Montazeri, N.; Pourshamsian, K.; Zoghi, R.; Mahjoob, S. Orient. J. Chem. 2012, 28, 103.
[78] Kumar, R.; Andhare, N. H.; Shard, A.; Richa.; Sinha, A. K. RSC Adv. 2014, 4, 19111.
[79] (a) Mason, T. J. Chem. Soc. Rev. 1997, 26, 443。
(b) Yu, X.; Chen, L.; Zhang, M.; Yi, T. Chem. Soc. Rev. 2014, 43, 5346.