吡咯烷酮衍生物的直接胺化: 构建偕二胺衍生物
收稿日期: 2014-10-11
修回日期: 2014-10-22
网络出版日期: 2014-10-23
基金资助
国家自然科学基金(Nos.21172162,21372174)和江苏省优势学科资助项目.
Direct Amination of N-Acyliminium Ion Surrogates: A Convenient Access to gem-Diamines Derivatives
Received date: 2014-10-11
Revised date: 2014-10-22
Online published: 2014-10-23
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21172162, 21372174) and the Project Funded by the Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions.
杨锦明 , 褚雪强 , 纪顺俊 . 吡咯烷酮衍生物的直接胺化: 构建偕二胺衍生物[J]. 有机化学, 2014 , 34(12) : 2462 -2470 . DOI: 10.6023/cjoc201410017
A novel 4-methylbenzenesulfonic acid (PTSA)-catalyzed intermolecular amination of N-acyliminium species with various N-sources via benzylic C(sp3)-O activation of functionalized 2-oxo-1-pyrrolidine derivatives has been developed. This method provides an efficient and chromatography-free access to gem-diamines equivalent with moderate to good yields. Because of the importance of gem-diamine derivatives, the methodology is expected to have a significant value for practical applications.
Key words： N-acyliminium ion; gem-diamines; green chemistry
[1] (a) Ricci, A. Modern Amination Reactions, Wiley-VCH, Weinheim, 2000. (b) Gobert, A.; Cara, B. D.; Cistarelli, L.; Millan, M. J. J. Pharmacol. Exp. Ther. 2003, 305, 338. (c) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921. (d) Lawrence, S. A. Amines: Synthesis Properties, and Applications, Cambridge University Press, Cambridge, UK, 2004. (e) Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795. (f) Lu, T.; Lu, Z.; Ma, Z.-X.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2013, 113, 4862.
[2] (a) Trost, B. M. Science 1991, 254, 1471. (b) Salvatore, R. N.; Yoon, C. H.; Jung, K. W. Tetrahedron 2001, 57, 7785. (c) Buchwald, S. L.; Mauger, C.; Mignani, G.; Scholz, U. Adv. Synth. Catal. 2006, 348. (d) Wuts, P. G. M.; Greene, T. W. Protective Groups in Organic Synthesis, 4th ed., Wiley-Interscience, New York, 2007. (e) Suzuki, K.; Hori, Y.; Kobayashi, T. Adv. Synth. Catal. 2008, 350, 652. (f) Long, T. R.; Maity, P. K.; Samarakoon, T. B.; Hanson, P. R. Org. Lett. 2010, 12, 2904.
[3] For selected reviews and examples see: (a) Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M. J. Adv. Synth. Catal. 2007, 349, 1555. (b) Guillena, G.; Ramon, D.; Yus, M. Chem. Rev. 2010, 110, 1611. (c) Rauws, T. R. M.; Maes, B. U. W. Chem. Soc. Rev. 2012, 41, 2463. (d) Shi, F.; Tse, M. K.; Zhou, S.; Pohl, M.-M.; Radnik, J.; Huebner, S.; Jaehnisch, K.; Brueckner, A.; Beller, M. J. Am. Chem. Soc. 2009, 131, 1775. (e) Bahn, S.; Imm, S.; Mevius, K.; Neubert, L.; Tillack, A.; Williams, J. M. J.; Beller, M. Chem.-Eur. J. 2010, 16, 3590.
[4] (a) Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681. (b) Suzuki, T. Chem. Rev. 2011, 111, 1825. (c) Hamid, M. H. S. A.; Allen, C. L.; Lamb, G. W.; Maxwell, A. C.; Maytum, H. C.; Watson, A. J. A.; Williams, J. M. J. J. Am. Chem. Soc. 2009, 131, 1766. (d) Shi, F.; Tse, M. K.; Cui, X.; Gordes, D.; Michalik, D.; Thurow, K.; Deng, Y.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 5912. (e) Michlik, S.; Kempe, R. Chem.-Eur. J. 2010, 16, 13193. (f) Watson, A. J. A.; Maxwell, A. C.; Williams, J. M. J. J. Org. Chem. 2011, 76, 2328. (g) Yu, X. C.; Liu, C. Z.; Jiang, L.; Xu, Q. Org. Lett. 2011, 13, 6184. (h) Zhang, E. L.; Tian, H. W.; Xu, S. D.; Yu, X. C.; Xu, Q. Org. Lett. 2013, 15, 2704. (i) Bala, M.; Verma, P. K.; Sharma, U.; Kumar, N.; Singh, B. Green Chem. 2013, 15, 1687.
[5] (a) Terrasson, V.; Marque, S.; Georgy, M.; Campagne, J.-M.; Prima, D. Adv. Synth. Catal. 2006, 348, 2063. (b) Motokura, K.; Nakagiri, N.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Org. Chem. 2007, 72, 6006. (c) Wang, G.-W.; Shen, Y.-B.; Wu, X.-L. Eur. J. Org. Chem. 2008, 4367. (d) Reddy, C. R.; Jithender, E. Tetrahedron Lett. 2009, 50, 5633. (e) Haubenreissera, S.; Niggemann, M. Adv. Synth. Catal. 2011, 353, 469. (f) Das, B. G.; Nallagonda, R.; Ghorai, P. J. Org. Chem. 2012, 77, 5577.
[6] (a) Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, S.; Minami, T.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124, 10968. (b) Qin, H.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2007, 46, 409. (c) Lu, Y.; Fu, X.; Chen, H.; Du, X.; Jia, X.; Liu, Y. Adv. Synth. Catal. 2009, 351, 1517. (d) Yamamoto, H.; Ho, E.; Namba, K.; Imagawa, H.; Nishizawa, M. Chem.-Eur. J. 2010, 16, 11271. (e) Ohshima, T.; Nakahara, Y.; Ipposhi, J.; Miyamotob, Y.; Mashima, K. Chem. Commun. 2011, 47, 8322.
[7] Fan, X.; Fu, L.-A.; Li, N.; Lv, H.; Cui, X.-M.; Qi, Y. Org. Biomol. Chem. 2013, 11, 2147.
[8] (a) Rubenbauer, P.; Bach, T. Adv. Synth. Catal. 2008, 350, 1125. (b) Powell, D. A.; Pelletier, G. Tetrahedron Lett. 2008, 49, 2495. (c) Feuerstein, M.; Laurenti, D.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2001, 42, 2313. (d) Deng, H.-P.; Wei, Y.; Shi, M. Eur. J. Org. Chem. 2011, 1956.
[9] For selected reviews and examples see: (a) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817. (b) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431. (c) Kinderman, S. S.; Wekking, M. M. T.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. J. Org. Chem. 2005, 70, 5519. (d) Raheem, I. T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404. (e) Pin, F.; Comesse, S.; Garrigues, B.; Marchalin, Š.; Daïch, A. J. Org. Chem. 2007, 72, 1181. (f) Muratore, M. E.; Holloway, C. A.; Pilling, A. W.; Storer, R. I.; Ttevitt, G.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 10796. (g) Martínez-Estibalez, U.; Gómez-SanJuan, A.; García-Calvo, O.; Aranzamendi, E.; Lete, E.; Sotomayor, N. Eur. J. Org. Chem. 2011, 3610. (h) Che, J.; Liu, Q.; Dai, X. Y.; Nie, L. L.; Wu, X. Y. Chin. J. Org. Chem. 2013, 33, 1 (in Chinese). (陈杰, 刘钦, 戴小鸯, 聂凛凛, 房辉辉, 吴小余, 有机化学, 2013, 33, 1.) (i) Ran, L. F.; Liang, H.; Guan, Z. H. Chin. J. Org. Chem. 2013, 33, 66 (in Chinese). (冉陇飞, 梁浩, 关正辉, 有机化学, 2013, 33, 66.) (j) Du, L.; Cao, P.; Liao, J. Acta Chim. Sinica 2013, 71, 1239 (in Chinese). (杜乐, 曹鹏, 廖建, 化学学报, 2013, 71, 1239.) (k) Nie, H. F.; Zhou, H. Y.; Li, X. N.; Li, Y. Q.; Wang, J. X. Chin. J. Org. Chem. 2013, 33, 2412 (in Chinese). (聂红芬, 周宏勇, 李小娜, 李云庆, 王家喜, 有机化学, 2013, 33, 2412.)
[10] (a) Carter, D. S.; Van Vranken, D. L. J. Org. Chem. 1999, 64, 8537. (b) Gunawan, S.; Hulme, C. Tetrahedron Lett. 2013, 54, 4467. (c) La Venia, A.; Lemrova, B.; Krchnak, V. ACS Comb. Sci. 2013, 15, 59.
[11] (a) Tsuchimoto, T.; Ozawa, Y.; Negoro, R.; Shirakawa, E.; Kawakami, Y. Angew. Chem. Int. Ed. 2004, 43, 4231. (b) Mentink, G.; van Maarseveen, J. H.; Hiemstra, H. Org. Lett. 2002, 4, 3497. (c) Othman, R. B.; Bousquet, T.; Othman, M.; Dalla, V. Org. Lett. 2005, 7, 5335. (d) Shirakawa, E.; Uchiyama, N.; Hayashi, T. J. Org. Chem. 2011, 76, 25. (e) Sun, M.-M.; Zhang, T.-S.; Bao, W.-L. J. Org. Chem. 2013, 78, 8155. (f) Xu, H.-Y.; Wang, S.-Y.; Jiang, R.; Xu, X.-P.; Chu, X.-Q.; Ji, S.-J. Tetrahedron 2012, 68, 8340.
[12] (a) Akiyama, S.; Niki, T.; Utsunomiya, T.; Watanabe, J.; Nishioka, M.; Suzuki, H.; Hayasaka, F.; Yamagishi, K. EP 1020447, 2000 [Chem. Abstr. 1999, 130, 237562]. (b) Gobert, J.; Giurgea, C.; Geerts, J.-P.; Bodson, G. EP 165919, 1985 [Chem. Abstr. 1986, 105, 97305]. (c) Kenda, B.; Quesnel, Y.; Ates, A.; Michel, P.; Turet, L.; Mercier, J. WO 2006128693, 2006 [Chem. Abstr. 2006, 146, 27722]. (d) Kenda, B.; Michel, P.; Quesnel, Y. WO 2005054188, 2005 [Chem. Abstr. 2005, 143, 59977]. (e) Gobert, J.; Geerts, J.-P.; Bodson, G. EP 0162036, 1985 [Chem. Abstr. 1985, 105, 18467]. (f) Schmiesing, R. J.; Murray, R. J. US 5334720, 1994 [Chem. Abstr. 1995, 122, 81126]. (g) Gouliaev, A. H.; Senning, A. Brain Res. Rev. 1994, 19, 180. (h) Ramachandran, G.; Karthikeyan, N. S.; Giridharan, P.; Sathiyanarayanan, K. I. Org. Biomol. Chem. 2012, 10, 5343.
[13] (a) Nishimura, Y. In Studies in Natural Products Chemistry, Vol. 16, Ed.: Atta-ur-Rahman, Elsevier, Amsterdam, 1995, 75. (b) Fletcher, M. D.; Campbell, M. M. Chem. Rev. 1998, 98, 763. (c) Kingsbury, W. D.; Boehm, J. C.; Perry, D.; Gilvary, C. Proc. Natl. Acad. Sci. U. S. A. 1984, 81, 4573. (d) Hwang, S. Y.; Berges, D. A.; Taggart, J. J.; Gilvarg, C. J. Med. Chem. 1989, 32, 694. (e) Nishimura, Y.; Shitara, E.; Adachi, H.; Toyoshima, M.; Nakajima, M.; Okami, Y.; Takeuchi, T. J. Org. Chem. 2000, 65, 2. (f) Lepper, E. R.; Ng, S. W.; Gutschow, M.; Weiss, M.; Hauschildt, S.; Hecker, T. K.; Luzzio, F. A.; Eger, K.; Figg, W. D. J. Med. Chem. 2004, 47, 2219.
[14] (a) Goodman, M.; Chorev, M. Acc. Chem. Res. 1979, 12, 1. (b) Chorev, M.; Goodman, M. Acc. Chem. Res. 1993, 26, 266. (c) Chorev, M.; Willson, C. G.; Goodman, M. J. Am. Chem. Soc. 1977, 99, 8075. (d) Moutevelis-Minakakis, P.; Photaki, I. J. J. Chem. Soc., Perkin Trans. 1 1985, 2277. (e) Katritzky, A. R.; Urogdi, L.; Mayence, A. J. Org. Chem. 1990, 55, 2206. (f) Zhao, M.; Kleinman, H. K.; Mokotoff, M. J. Pept. Res. 1997, 49, 240.
[15] (a) Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2005, 127, 15696. (b) Liang, Y.; Rowland, E. B.; Rowland, G. B.; Perman, J. A.; Antilla, J. C. Chem. Commun. 2007, 4477. (c) Cheng, X.; Vellalath, S.; Goddard, R.; List, B. J. Am. Chem. Soc. 2008, 130, 15786.
[16] 16. Zhu, S. J.; Dong, J.; Fu, S. M.; Jiang, H. F.; Zeng, W. Org. Lett. 2011, 13, 4914.
[17] (a) Barker, J.; Kilner, M. Coord. Chem. Rev. 1994, 133, 219. (b) Lee, M. Y.; Kim, M. H.; Kim, J.; Kim, S. H.; Kim, B. T.; Jeong, I. H.; Chang, S.; Kim, S. H.; Chang, S.-Y. Bioorg. Med. Chem. Lett. 2010, 20, 541. (c) Vernier, W.; Chong, W.; Rewolinski, D.; Greasley, S.; Pauly, T.; Shaw, M.; Dinh, D.; Ferre, R. A.; Nukui, S.; Ornelas, M.; Reyner, E. Bioorg. Med. Chem. 2010, 18, 3307. (d) Al-Said, M. S.; Ghorab, M. M.; Al-Dosari, M. S.; Hamed, M. M. Eur. J. Med. Chem. 2011, 46, 201.(a) Gonzlez, A. S.; Arrays, R. G.; Carretero, J. C. Org. Lett. 2006, 8, 2977. (b) Morimoto, H.; Lu, G.; Aoyama, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 9588.
/
| 〈 |
|
〉 |
