Chinese Journal of Organic Chemistry >
Structure of the Condensed Product of Aromatic o-Aminonitrile with Carbonyl Compound and Its Mechanism
Received date: 2014-06-06
Revised date: 2014-07-16
Online published: 2014-08-26
Supported by
Project supported by the Basic Research Fund of Beijing Institute of Technology (No. 2012CX100035).
Friedländer reaction is one of the most important routes to synthesize the quinoline and its derivatives, which possesses excellent bioactivity and photo-electricity activity. Recently, a new skeleton product besides the normal Friedländer quinoline was discovered by the condensation of aromatic o-aminonitrile and carbonyl compounds, and this phenomenon has attracted many researchers, but the skeleton structure of new conversion is debated. Herein, this paper reviews on the development progress of this new kind reaction. According to recent research results, the skeleton structure of new conversion was assigned as quinazolinone, which was confirmed by the 13C NMR, FT-IR, and single-crystal X-ray diffraction deterimations. Therefore, this new conversion is abbreviated as PDF conversion, which means a new conversion from Pinner to Dimroth rearrangement in the Friedländer reaction. The total reaction mechanism of o-aminonitrile with carbonyl compound was proposed.
Yang Junjuan , Shi Daxin , Liu Mingxing , Zhang Lijun , Zhang Qi , Li Jiarong . Structure of the Condensed Product of Aromatic o-Aminonitrile with Carbonyl Compound and Its Mechanism[J]. Chinese Journal of Organic Chemistry, 2014 , 34(12) : 2424 -2437 . DOI: 10.6023/cjoc201406007
[1] Richter, M.; Molnár, J.; Hilgeroth, A. J. Med. Chem. 2006, 49, 2838.
[2] Elnagdi, M. H.; Erian, A. W. W. Arch. Pharm. 1991, 324, 853.
[3] Ferris, J. P.; Orgel, L. E. J. Am. Chem. Soc. 1966, 88, 3829.
[4] Dias, A. M.; Cabral, I.; Proença, M. F.; Booth, B. L. J. Org. Chem. 2002, 67, 5546.
[5] Taylor, E. C.; Wachsen, E. J. Org. Chem. 1978, 43, 4154.
[6] Erian, A. W. Chem. Rev. 1993, 93, 1991.
[7] Abdelrazek, F. M.; Bahbouh, M. S.; Jordan, J. Earth Environ. Sci. 2012, 4, 47.
[8] Camps, P.; Gómez, E.; Muñoz, Torrero, D.; Badia, A.; Vivas, N. M.; Barril, X.; Orozco, M.; Luque, F. J. J. Med. Chem. 2001, 44, 4733.
[9] McKenna, M. T.; Proctor, G. R.; Young, L. C.; Harvey, A. L. J. Med. Chem. 1997, 40, 3516.
[10] Barreiro, E. J.; Camara, C. A.; Verli, H.; Brazil, Mas, L.; Castro, N. G.; Cintra, W. M.; Aracava, Y.; Rodrigues, C. R.; Fraga, C. A. J. Med. Chem. 2003, 46, 1144.
[11] Li, J.-R.; Ma, S.-L. Chin. Chem. Lett. 2005, 16, 1424 (in Chinese). (李加荣, 马淑玲, 中国化学快报, 2005, 16, 1424.)
[12] Zhen, B.; Jiao, Q.; Zhang, Y.; Wu, Q.; Li, H. S.; Shi, D. X.; Li, J. R. Catal. Commun. 2013, 32, 1.
[13] Yang, L.-P.; Li, J.-R.; Chai, H.-X.; Yuan, H.; Zhang, Q.; Shi, D.-X. Chin. J. Org. Chem. 2013, 33, 174 (in Chinese). (杨留攀, 李加荣, 柴红新, 袁洪, 张奇, 史大昕, 有机化学, 2013, 33, 174.)
[14] Yang, D. L.; Shi, D. X.; Zhang, Q.; Chai, H. X.; Li, J. R. Acta Crystallogr., Sect. B: Struct. Sci. 2013, 69, o633.
[15] Yang, D.-L.; Li, J.-R.; Sun, K.-N.; Lu, H.-Y.; Liu, M.-X.; Shi, D.-X. Chin. J. Org. Chem. 2013, 33, 2341 (in Chinese). (杨德利, 李加荣, 孙克宁, 路红燕, 刘明星, 史大昕, 有机化学, 2013, 33, 2341.)
[16] Yang, L. P.; Shi, D. X.; Chen, S.; Chai, H. X.; Huang, D. F.; Zhang, Q.; Li, J. R. Green Chem. 2012, 14, 945.
[17] Tang, J. H.; Li, J. R.; Zhang, L.; Ma, S. L.; Shi, D. X.; Zhang, Q.; Yang, L. P.; Wang, X.; Liu, X.; Liu, C. J. Heterocycl. Chem. 2012, 49, 533.
[18] Liu, C.-E.; Tang, J.-H.; Li, J.-R. Chin. J. Org. Chem. 2012, 32, 532 (in Chinese). (刘长娥, 唐建红, 李加荣, 有机化学, 2012, 32, 532.)
[19] Liu, X.; Shi, D. X.; Tang, J. H.; Yang, D. L. Acta Crystallogr., Sect. E: Struct. Sci. 2011, 67, o2016.
[20] Tang, J. H.; Shi, D. X.; Yan, L. P.; Liu, X.; Li, J. R. Acta Crystallogr., Sect. B: Struct. Sci. 2011, 67, o1672.
[21] Li, J. R.; Chen, X.; Shi, D. X.; Ma, S. L.; Li, Q.; Zhang, Q.; Tang, J. H. Org. Lett. 2009, 11, 1193.
[22] Li, J. R.; Zhang, L.; Shi, D. X.; Li, Q.; Wang, D.; Wang, C.; Zhang, Q.; Fan, Y. Synlett 2008, 233.
[23] Wu, X. F.; Oschatz, S.; Block, A.; Spannenberg, A.; Langer, P. Org. Biomol. Chem. 2014, 12, 1865.
[24] Gyuris, M.; Puskas, L. G.; Toth, G. K.; Kanizsai, I. Org. Biomol. Chem. 2013, 11, 6320.
[25] Kanawade, S. B.; Patil, S. P.; Nikam, P. S.; Gangurde, S. A.; Jachak, M. N.; Toche, R. B. J. Heterocycl. Chem. 2012, 49, 363.
[26] Majumdar, K. C.; Roy, B.; Debnath, P.; Taher, A. Curr. Org. Chem. 2010, 14, 846.
[27] Marco-Contelles, J.; Pérez-Mayoral, E.; Samadi, A.; Carreiras, M. C.; Soriano, E. Chem. Rev. 2009, 109, 2652.
[28] Shaban, M. E.; Youssef, A. M.; Elaasar, N. K.; EI-Ziaty, A. K. Pak J. Sci. Ind. Res. 2008, 51, 119.
[29] Kouznetsov, V. V.; Mendez, L. Y.; Gomez, C. M. Curr. Org. Chem. 2005, 9, 141.
[30] Riesgo, E. C.; Jin, X.; Thummel, R. P. J. Org. Chem. 1996, 61, 3017.
[31] Yang, D.; Jiang, K.; Li, J.; Xu, F. Tetrahedron 2007, 63, 7654.
[32] Palimkar, S. S.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2003, 68, 9371.
[33] Dormer, P. G.; Eng, K. K.; Farr, R. N.; Humphrey, G. R.; McWilliams, J. C.; Reider, P.; Sager, J. W.; Volante, R. J. Org. Chem. 2003, 68, 467.
[34] Cheng, C. C.; Yan, S. J. Org. React. 1982, 28.
[35] Muchowski, J. M.; Maddox, M. L. Can. J. Chem. 2004, 82, 461.
[36] Leon, R.; Garcia, A. G.; Marco-Contelles, J. J. Chem. Res. 2006, 8, 536.
[37] Rane, B. S.; Kazi, M. A.; Bagul, S. M.; Shelar, D. P.; Toche, R. B.; Jachak, M. N. J. Fluoresc. 2010, 20, 415.
[38] Perez-Mayoral, E.; Musilova, Z.; Gil, B.; Marszalek, B.; Polozij, M.; Nachtigall, P.; Cejka, J. Dalton Trans. 2012, 41, 4036.
[39] Zhang, L. J.; Yu, J. L.; Wang, W. L.; Li, H.; Xu, D. D.; Bi, Y. D.; Liu, F. D. Tetrahedron Lett. 2014, 55, 710.
[40] Safari, J.; Gandomi-Ravandi, S. C. R. Chim. 2013, 16, 1158.
[41] Nguyen, T. B.; Ermolenko, L.; Al-Mourabit, A. Green Chem. 2013, 15, 2713.
[42] Labade, V. B.; Shinde, P. V.; Shingare, M. S. Tetrahedron Lett. 2013, 54, 5778.
[43] Desroses, M.; Scobie, M.; Helleday, T. New J. Chem. 2013, 37, 3595.
[44] Sharma, R.; Pandey, A. K.; Chauhan, P. M. S. Synlett 2012, 23, 2209.
[45] Ghashang, M. Orient. J. Chem. 2012, 28, 1213.
[46] Spagnol, G.; Rajca, A.; Rajca, S. J. Org. Chem. 2007, 72, 1867.
[47] Bonne, D.; Dekhane, M.; Zhu, J. Org. Lett. 2005, 7, 5285.
[48] Klemm, L. H.; Weakley, T. J. R.; Gilbertson, R. D.; Song, Y. H. J. Heterocycl. Chem. 1998, 35, 1269.
[49] Zhang, L. J.; Li, J. R.; Shi, D. X.; Chen, J. Acta Crystallogr., Sect. E: Struct. Sci. 2008, 64, o449.
[50] Zhang. L.; Shi, D. X.; Li, J. R.; Zhang, L.; Fan, Y. Q. Acta Crystallogr., Sect. E: Struct. Sci. 2008, 64, o1056.
[51] Zhang, L.; Shi, D. X.; Fan, Y. Q.; Qian, D.; Li, J. R. Acta Crystallogr., Sect. E: Struct. Sci. 2009, 65, o1345
[52] Zhang, L.; Li, J. R.; Yang, X.; Shi, D. X.; Chen, J. Acta Crystallogr., Sect. E: Struct. Sci. 2008, 64, o450.
[53] Zhang, L. J.; Li, J. R.; Shi, D. X.; Zhang, L.; Fan, Y. Q. Acta Crystallogr., Sect. E: Struct. Sci. 2008, 64, o448.
[54] Li, J.-R.; Zhang, L.-J.; Shi, D.-X.; Zhang, Q. Chin. Chem. Lett. 2008, 19, 15 (in Chinese). (李加荣, 张立军, 史大昕, 张奇, 中国化学快报, 2008, 19, 15.)
[55] Chao, X.; He, X.; Yang, Y.; Zhou, X.; Jin, M.; Liu, S.; Cheng, Z.; Liu, P.; Wang, Y.; Yu, J.; Tan, Y.; Huang, Y.; Qin, J.; Rapposelli, S.; Pi, R. Bioorg. Med. Chem. Lett. 2012, 22, 6498.
[56] Gutschow, M.; Neumann, U.; Sieler, J.; Eger, K. Pharm. Acta Helv. 1998, 73, 95.
[57] Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. 1995, 34, 1555.
[58] Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr., Sect. E: Struct. Sci. 1990, 46, 256.
[59] Li, J. R.; Ma, S. L.; Sun, Y. J.; Wei, X. J.; Zhou, Z. M. J. Heterocycl. Chem. 2006, 43, 745.
[60] Li, J.-R.; Sun, Y.-J.; Zhou, Z.-M. Chin. J. Org. Chem. 2006, 26, 928 (in Chinese). (李加荣, 马淑玲, 孙永江, 周智明, 有机化学, 2006, 26, 928.)
[61] Shi, D.; Dou, G.; Zhou, Y. Synthesis-Stuttgart 2008, 13, 2000.
[62] Shi, D. Q.; Rong, L. C.; Wang, J. X.; Zhuang, Q. Y.; Wang, X. S.; Hua, H. W. Tetrahedron Lett. 2003, 44, 3199.
[63] Cheng, X.; Vellalath, S.; Goddard, R.; List, B. J. Am. Chem. Soc. 2008, 130, 15786.
[64] Chinigo, G. M.; Paige, M.; Grindrod, S.; Hamel, E.; Dakshanamurthy, S.; Chruszcz, M.; Minor, W.; Brown, M. L. J. Med. Chem. 2008, 51, 4620.
[65] Diwu, Z.; Lu, Y.; Upson, R. H.; Zhou, M.; Klaubert, D. H.; Haugland, R. P. Tetrahedron 1997, 53, 7159.
[66] Zappalà, M.; Grasso, S.; Micale, N.; Zuccalà, G.; Menniti, F. S.; Ferreri, G.; De, S. G.; De, M. C. Bioorg. Med. Chem. Lett. 2003, 13, 4427.
[67] Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787.
[68] He, F.; Snider, B. B. J. Org. Chem. 1999, 64, 1397.
[69] Siskos, A. P.; Hill, A. M. Tetrahedron Lett. 2003, 44, 789.
[70] Zaki, M. Molecules 1998, 3, 71.
[71] Elkholy, Y. M.; Morsy, M. A. Molecules 2006, 11, 890.
[72] Angelin, M.; Vongvilai, P.; Fischer, A.; Ramström, O. Chem. Commun. 2008, 6, 768.
[73] Angelin, M.; Fischer, A.; Ramström, O. J. Org. Chem. 2008, 73, 3593.
[74] Lajoie, G.; Lepine, F.; Maziak, L.; Belleau, B. Tetrahedron Lett. 1983, 24, 3815.
[75] Neugebauer, W.; Pinet, E.; Kim, M.; Carey, P. R Can. J. Chem. 1996, 74, 341.
[76] Luzyanin, K. V.; Kukushkin, V. Y.; Kuznetsov, M. L.; Garnovskii, D. A.; Haukka, M.; Pombeiro, A. J. Inorg. Chem. 2002, 41, 2981.
[77] Wang, J.; Wang, J.; Zhu, Y.; Lu, P.; Wang, Y. Chem. Commun. 2011, 47, 3275.
[78] Lin, G.-C.; Liu, L.; Zhang, L.- R.; Zhang, L.-H. Chin. J. Inorg. Chem. 2002, 10, 405 (in Chinese). (林桂椿, 刘莉, 张亮仁, 张礼和, 合成化学, 2002, 10, 405.)
[79] Kurz, T.; Widyan, K.; Wackendorff, C.; Schlüter, K. Synthesis 2004, 1987.
[80] Liu, X.; Shi, D.-X.; Tang, J.-H.; Zhang, Q.; Li, J.-R. Chin. J. Org. Chem. 2011, 31, 1710 (in Chinese). (刘璇, 史大昕, 唐建红, 张奇, 李加荣, 有机化学, 2011, 31, 1710.)
[81] Zhang, P. W.; Terefenko, E. A.; Fensome, A.; Wrobel, J.; Winneker, R.; Lundeen, S.; Marschke, K. B.; Zhang, Z. M. J. Med. Chem. 2002, 45, 4379.
[82] Kamal, A.; Ramana, K. V.; Rao, M. V. J. Org. Chem. 2001, 66, 997.
[83] Yang, L. P.; Li, J. R.; Chai, H. X.; Lu, H. Y.; Zhang, Q.; Shi, D. X. Chin. J. Chem. 2013, 31, 443.
/
| 〈 |
|
〉 |
