Chinese Journal of Organic Chemistry >
A New Procedure for Synthesizing 4,5-Dimethyl-2-(trimethylsilyl)-thiophene-3-carboxamide Derivatives
Received date: 2014-06-06
Revised date: 2014-06-20
Online published: 2014-07-03
Supported by
Project supported by the National Food Production Technology Project of China during the Twelfth Five-Year Period (Nos.2011BAD16B07, 2012BAD04B07), and the Modern Agriculture Demonstration and Regional Innovation Cluster Plan Project of the Chinese Academy of Sciences (No.CXJQ120111).
A new procedure for synthesizing 4,5-dimethyl-2-(trimethylsilyl)thiophene-3-carboxamide derivatives was explored. Using commercially available 3-mercaptobutan-2-one and methyl propiolate as starting materials, the target compounds were obtained in four steps via silylanization of methyl propiolate, cyclization, selective hydrolysis and amidation. And the promoters involved in silylanization, cyclization and selective hydrolysis were screened. The procedure exhibited several advantages such as easily available raw materials, mild reaction conditions, easily purified intermediates and high single-step yields. It had potential to be applied to scale production.
Key words： silylanization; cyclization; selective hydrolysis; synthesis
Jin Wenbo , Xie Guiying , Sun Shujun , Zhao Yanqin , Cheng Yi-nan , Sun Bingjian , Li Honglian . A New Procedure for Synthesizing 4,5-Dimethyl-2-(trimethylsilyl)-thiophene-3-carboxamide Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(11) : 2376 -2381 . DOI: 10.6023/cjoc201406006
[1] Phillion, D. P.; Sant, K. A. V.; Walker, D. M. WO 9524380, 1995 [Chem. Abstr. 1995, 124, 116873].
[2] Phillion, D. P.; Braccolino, D. S.; Graneto, M. J.; Phillips, W. G.; Sant, K. A. V.; Walker, D. M.; Wong, S. C. EP 538231, 1993 [Chem. Abstr. 1993, 119, 160256].
[3] Phillion, D. P.; Graneto, M. J.; Pratt, J. K.; Wong, S. C. CA 2121917, 1994 [Chem. Abstr. 1995, 122, 213924].
[4] Phillion, D.; Wong, S. C.; Shortt, B. US 5486621, 1996 [Chem. Abstr. 1996, 124, 253325].
[5] Xie, G. Y.; Jin, W. B.; Zhao, Y. Q.; Cheng, Y. N.; Sun, B. J.; Sun, S. J.; Wang, M. Z.; Wei D. D.; Li, H. L. Chin. J. Org. Chem. 2014, 34, 1124 (in Chinese).(谢桂英, 靳文波, 赵艳芹, 程绎南, 孙炳剑, 孙淑君, 汪梅子, 位丹丹, 李洪连, 有机化学, 2014, 34, 1124.)
[6] Li, L.; Gu, F. L.; Zhu, K.; Qiu, H. Y. J. Hangzhou Normal Univ. (Nat. Sci.) 2011, 10, 52 (in Chinese). (李莉, 顾峰雷, 诸坤, 邱化玉, 杭州师范大学学报(自然科学版), 2011, 10, 52.)
[7] Hu, Y. G.; Lu, M. Y.; Song, H. L.; Ding, M. W. Chin. J. Org. Chem. 2005, 25, 295 (in Chinese). (胡扬根, 吕茂云, 宋鹤丽, 丁明武, 有机化学, 2005, 25, 295.)
[8] Liao, Q. B.; Liu, M. G.; Yu, L.; Zhu, M.; Ding, M. W. Chin. J. Org. Chem. 2009, 29, 1582 (in Chinese). (廖全斌, 刘明国, 喻兰, 朱敏, 丁明武, 有机化学, 2009, 29, 1582.)
[9] Phillips, G.; Fevig, T. L.; Lau, P. H.; Klemm, G. H.; Mao, M. K.; Ma, C.; Gloeckner, J. A.; Clark, A. S. Org. Proc. Res. Dev. 2002, 6, 357.
[10] Fevig, T. L.; Pillips, W. G.; Lau, P. H. J. Org. Chem. 2001, 66, 2493.
[11] Pillips, W. G.; Mao, M. K.; Ma, C.; Fevig, T. WO 9962915, 1999 [Chem. Abstr. 1999, 132, 23082]
[12] Lu, B.; Falck, J. R. Angew. Chem., Int. Ed. 2008, 47, 7508.
[13] Ihara, H.; Koyanagi, M.; Suginome, M. Org. Lett. 2011, 13(10), 2662.
[14] Alexey, K.; Yoshiharu, O.; Yoshihiro, I.; Vladimir, G. Org. Lett. 2013, 15(10), 2498.
[15] Ureshino, T.; Yoshida, T.; Kuninobu, Y.; Takai, K. J. Am. Chem. Soc. 2010, 132, 14324.
[16] Mannam, S.; Sekar, G. Tetrahedron Lett. 2008, 49, 2457.
[17] Shi, M.; Wang, C. J. J. Chem. Res. 2004, 107.
[18] Hermeling, D.; Schafer, H. J. Chem. Ber. 1988, 121, 1151.
[19] Stohrer, J.; Fritz-Langhals, E.; Bruninghaus, C. US 0059154, 2004 [Chem. Abstr. 2004, 140, 199022].
[20] Sugita, H.; Hatanaka, Y.; Hiyama, T. Synlett 1996, 637.
[21] Yamaguchi, M.; Hayashi, A.; Minami, T. J. Org. Chem. 1991, 56(13), 4091.
[22] Jiang, H. L.; Zhu, S. Z. Tetrahedron Lett. 2005, 46, 517.
[23] Andreev, A. A.; Konshin, V. V.; Komarov, N. V.; Rubin, M.; Brouwer, C.; Gevorgyan, V. Org. Lett. 2004, 6(3), 421.
[24] Sugita, H.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1995, 36(16), 2769.
[25] Dunn, P. J.; Rees, C. W.; J. Chem. Soc., Perkin Trans. 1 1987, 1585.
[26] Coppola, G. M.; Damon, R. E. J. Heterocycl. Chem. 1995, 32, 1133.
[27] Rankin, T.; Tykwinski, R. R. Org. Lett. 2003, 5(2), 213.
[28] Wasserman, H. H.; Frechette, R.; Oida, T.; Van Duzer, J. H. J. Org. Chem. 1989, 54(26), 6012.
[29] McCulloch, A. W.; McInnes, A. G. Can. J. Chem. 1974, 52, 3569.
[30] Bohlmann, F.; Bresinsky, E. Chem. Ber. 1964, 97(8), 2109.
[31] Baharfar, R.; Hossein nia, R.; Baghbanian, S. M. Lett. Org. Chem. 2008, 5, 128.
[32] Baharfar, R.; Baghbaniana, S. M.; Hossein N, R.; Bijanzadeh, H. R. Lett. Org. Chem. 2007, 4, 567.
[33] Roth, F.; Gygax, P.; Fráter, G. Tetrahedron Lett. 1992, 33, 1045.
[34] Matsuya, Y.; Hayashi, K.; Wada, A.; Nemoto, H. J. Org. Chem. 2008, 73(5), 1987.
[35] Reddy, L. R.; Saravanan, P.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 6230.
[36] Downey, C. W.; Craciun, S.; Neferu, A. M.; Vivelo, C. A.; Mueller, C. J.; Southall, B. C.; Corsi, S.; Etchill, E. W.; Sault, R. J. Tetrahedron Lett. 2012, 53, 5763.
[37] Khurana, J. M.; Chauhan, S.; Bansal, G. Monatsh. Chem. 2004, 135, 83.
[38] Stanetty, P.; Puschautz, E. Monatsh. Chem. 1989, 120, 65.
[39] Hawker, D. D.; Silverman, R. B. Bioorg. Med. Chem. 2012, 20, 5763.
[40] Node, M.; Nishide, K.; Sai, M.; Fuji, K.; Fujita, E. J. Org. Chem. 1981, 46, 1991.
[41] Tsuji, T.; Rataoka, T.; Yoshioka, M.; Sendo, Y.; Hirai, Y. N. S.; Maeda, T.; Nagata, W. Tetrahedron Lett. 1979, 30, 2793.
[42] Wei, B. M.; Zhang, Z. Y.; Dai, Z. Q.; Zhang, K. C. Monatsh. Chem. 2011, 142, 1029.
[43] Gogoi, P.; Konwar, D.; Sharma, S. D. Synth. Commun. 2006, 36, 1259.
[44] Akiyama, T.; Hirofuji, H.; Hirose, A.; Ozaki, S. Synth. Commun. 1994, 24(15), 2179.
[45] Lian, X. Y.; Fu, S. M.; Ma, T. M.; Li S. B.; Zeng, W. Appl. Organomet. Chem. 2011, 25, 443.
[46] Wu, Y. Q.; Limburg, D. C.; Wilkinson, D. E.; Vaal, M. J.; Hamilton, G. S. Tetrahedron Lett. 2000, 41, 2847.
[47] Jung, M. E.; Lyster, M. A. J. Am. Chem. Soc. 1977, 99(3), 968.
[48] Keinan, E.; Sahai, M. J. Org. Chem. 1990, 55, 3922.
[49] Cossy, J.; Albouy, A.; Scheloske, M.; Pardo, D. G. Tetrahedron Lett. 1994, 35(10), 1539.
/
| 〈 |
|
〉 |
