Synthesis of N-Substituted Pyrroles Catalyzed by Bromodimethylsulfonium Bromide

doi:10.6023/cjoc201307026

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (1): 190-196.DOI: 10.6023/cjoc201307026 Previous Articles Next Articles

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溴化二甲基溴化硫催化下合成N-取代吡咯类化合物

岳闽敏, 刘巨艳, 王英, 袁斌

天津师范大学化学学院天津市功能分子结构与性能重点实验室无机-有机杂化功能材料化学省部共建教育部重点实验室天津 300387

收稿日期:2013-07-17 修回日期:2013-09-02 发布日期:2013-09-06
通讯作者: 刘巨艳,王英 E-mail:hxxyljy@mail.tjnu.edu.cn
基金资助:
天津市自然科学基金（Nos. 12JCZDJC34300，11JCYBJC03600）；青年科学基金（No. 21001080）资助项目.

Synthesis of N-Substituted Pyrroles Catalyzed by Bromodimethylsulfonium Bromide

Yue Minmin, Liu Juyan, Wang Ying, Yuan Bin

Tianjin Key Laboratory of Structure and Performance for Functional Molecule, Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, Ministry of Education, College of Chemistry, Tianjin Normal University, Tianjin 300387

Received:2013-07-17 Revised:2013-09-02 Published:2013-09-06
Supported by:
Project supported by the Natural Science Foundation of Tianjin City (Nos. 12JCZDJC34300, 11JCYBJC03600), the Young Scientist Fund (No. 21001080).

Cite this article

Yue Minmin, Liu Juyan, Wang Ying, Yuan Bin. Synthesis of N-Substituted Pyrroles Catalyzed by Bromodimethylsulfonium Bromide[J]. Chin. J. Org. Chem., 2014, 34(1): 190-196.

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[1] (a) Kohling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213.

(b) Yang, S.; Denny, W. A. J. Org. Chem. 2002, 67, 8958.

(c) Caron, S.; Vazquez, E. J. Org. Chem. 2003, 68, 4104.

(d) Jiang, B.; Yang, C.; Wang, J. J. Org. Chem. 2002, 67, 1396.

(e) Bringmann, G.; Tasler, S.; Endress, H.; Muhlbacher, J. Chem. Commun. 2001, 761.

[2] (a) Rosenbaum, C.; Katzka, C.; Marzinzik, A. H.; Waldmann, H. Chem. Commun. 2003, 1822.

(b) Abid, B. M.; London, G.; Esquibel, J.; Török, M.; Mhadgut, S. C.; Yan, P.; Prakash, G. K. S. Angew. Chem., Int. Ed. 2005, 44, 3086.

(c) Kremsnerm, J. M.; Kappe, C. O. Eur. J. Org. Chem. 2005, 3672.

[3] (a) Knorr, L. Ber. 1884, 17, 1635.

(b) Kleinspehn, G. G. J. Am. Chem. Soc. 1955, 77, 1546.

[4] Hantzsch, A. Ber. 1890, 23, 1474.

[5] (a) Knorr, L. Ber. 1884, 17, 2863.

(b) Paal, C. Ber. 1884, 17, 2756.

[6] Banik, B. K.; Samajdar, S.; Banik, I. J. Org. Chem. 2004, 69, 213.

[7] Danks, T. N. Tetrahedron Lett. 1999, 40, 3957.

[8] Rao, H. S. P.; Jothilingam, S.; Scheeren, H. W. Tetrahedron 2004, 60, 1625.

[9] Banik, B. K.; Banik, I.; Renteria, M.; Dasgupta, S. K. Tetrahedron Lett. 2005, 46, 2643.

[10] Chen, J.; Wu, H.; Zheng, Z.; Jin, C.; Zhang, X.; Su, W. Tetrahedron Lett. 2006, 47, 5383.

[11] Klappa, J. J.; Rich, A. E.; McNeill, K. Org. Lett. 2002, 4, 435.

[12] Curini, M.; Montanari, F.; Rosati, O.; Lioy, E.; Margarita, R. Tetrahedron Lett. 2003, 44, 3923.

[13] Fuerstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637.

[14] Periasamy, M.; Srinivas, G.; Bharathi, P. J. Org. Chem. 1999, 64, 4204.

[15] Dieter, R. K.; Yu, H. Org. Lett. 2000, 2, 2283.

[16] Arcadi, A.; Rossi, E. Tetrahedron 1998, 54, 15253.

[17] Lee, C. F.; Yang, L. M.; Hwu, T. Y.; Feng, A. S.; Tseng, J. C.; Luh, T. Y. J. Am. Chem. Soc. 2000, 122, 4992.

[18] Dou, G.; Shi, C.; Shi, D. J. Comb. Chem. 2008, 10, 810.

[19] Bharadwaj, A. R.; Scheidt, K. A. Org. Lett. 2004, 6, 2465.

[20] Katritzky, A.; Jiang, J.; Steel, P. J. J. Org. Chem. 1994, 59, 4551.

[21] Veisi, H.; Hemmati, S.; Veisi, H. J. Chin. Chem. Soc. 2009, 56, 240.

[22] Sreekumar, R.; Padmakumar, R. Synth. Commun. 1998, 28, 1661.

[23] De, D.; Mague, J. D.; Byers, L. D.; Krogstad, D. J. Tetrahedron Lett. 1995, 36, 205.

[24] (a) Tfxier-Boullet, F.; Klein, B.; Hamelin, J. Synthesis 1986, 409.

(b) Kidwai, K.; Singhal, K.; Rastogi, S. J. Heterocycl. Chem. 2006, 43, 1231.

[25] (a) Raghavan, S.; Anuradha, K. Synlett 2003, 711.

(b) Zhu, X. H.; Chen, G.; Xu, Z. L. Chin. J. Org. Chem. 2008, 28, 115.

[26] Drewes, S. E.; Hogan, C. J. Synth. Commun. 1989, 19, 2101.

[27] Shaw, D. J.; Wood, W. F. J. Chem. Educ. 1992, 69, A313.

[28] (a) Samajdar, S.; Becker, F. F.; Banik, B. K. Heterocycles 2001, 55, 1019.

(b) Abid, M.; Spaeth, A.; Török, B. Adv. Synth. Catal. 2006, 348, 2191.

[29] Wang, B.; Gu, Y.; Luo, C.; Yang, T.; Yang, L.; Suo, J. Tetrahedron Lett. 2004, 45, 3417.

[30] De, K.; Surya, K. Catal. Lett. 2008, 124, 174.

[31] Chen, J. X.; Liu, M. C.; Yang, X. L.; Ding, J. C.; Wu, H. Y. J. Braz. Chem. Soc. 2008, 19(5), 877.

[32] Armugam, P.; Perumal, P. T. Chem. Lett. 2006, 35, 632.

[33] Abbas, T.; Najafi, C. A. Chin. J. Chem. 2012, 30, 372.

[34] Han, F. G.; Lu, Y.; Ji, X. M.; Zhao, M. Q.; Zhang, X. Y.; Liu, Y. Chin. J. Org. Chem. 2010, 30, 1080.

[35] (a) Veisi, H. Tetrahedron Lett. 2010, 51, 2109.

(b) Luo, H.; Kang, Y.; Li, Q.; Yang, L. Heteroat. Chem. 2008, 19 (6), 592.

[36] Yadav, J. S.; Reddy, B. V. S.; Eeshwaraiah, B.; Gupta, M. K. Tetrahedron Lett. 2004, 45, 5873.

[37] Zhang, Z. H.; Li, J. J.; Li, T. S. Ultrason. Sonochem. 2008, 15, 673.

[38] (a) Choudhury, L. H.; Pravin, T.; Khan, A. T. Tetrahedron 2009, 65, 9513.

(b) Olah, G. A.; Vankar, Y. D.; Arvanaghi, M.; Surya Prakash, G. K. Synthesis 1979, 720.

(c) Furukawa, N.; Inoue, T.; Aida, T.; Oae, S. J. Chem. Soc., Chem. Commun. 1973, 212a.

[39] Meerwein, H.; Zenner, K. F.; Gipp, R. Justus Liebigs Ann. Chem. 1965, 67, 688.

[40] (a) Choudhury, L. H. Synlett 2006, 1619.

(b) Khan, A. T.; Ali, A. M.; Goswami, P.; Choudhury, L. H. J. Org. Chem. 2006, 71, 8961.

(c) Das, B.; Krishnaiah, M.; Katta, V. Tetrahedron Lett. 2006, 47, 4457.

(d) Khan, A. T.; Mondal, E.; Borah, B. M.; Ghosh, S. Eur. J. Org. Chem. 2003, 4113.

(e) Khan, A. T.; Islam, S.; Majee, A.; Chattopadhyay, T.; Ghosh, S. J. Mol. Catal., A: Chem. 2005, 239, 158.

(f) Khan, A. T.; Sahu, P. R.; Majee, A. J. Mol. Catal., A: Chem. 2005, 226, 207.

(g) Khan, A. T.; Mondal, E.; Ghosh, S.; Islam, S. Eur. J. Org. Chem. 2004, 2002.

(h) Das, B.; Holla, H.; Srinivas, Y. Tetrahedron Lett. 2007, 48, 61.

[41] (a) Liu, J. Y.; Liu, J.; Wang, J. D.; Jiao, D. Q.; Liu, H. W. Synth. Commun. 2010, 40, 2047.

(b) Liu, J. Y.; Cao, G. E.; Xu, W.; Cao, J.; Wang, W. L. Appl. Organomet. Chem. 2010, 24, 685.

(c) Liu, J. Y.; Liu, Q.; Xu, W.; Wang, W. L. Chin. J. Chem. 2011, 29, 1739.

(d) Zhang, L. J.; Liu, J. Y.; Wang, Y. Chin. J. Org. Chem. 2013, 33, 339.

[42] Ali, R. Appl. Organomet. Chem. 2011, 25, 585.

溴化二甲基溴化硫催化下合成N-取代吡咯类化合物

Synthesis of N-Substituted Pyrroles Catalyzed by Bromodimethylsulfonium Bromide

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