研究论文

溴化二甲基溴化硫催化下吡唑稠合型异香豆素的合成

  • 房智兴 ,
  • 刘巨艳 ,
  • 乔艳红
展开
  • 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: 2018-03-14

  修回日期: 2018-05-05

  网络出版日期: 2018-05-24

基金资助

天津市自然科学基金(No.12JCZDJC34300)、大学生创业训练(No.201447)资助项目.

Bromodimethylsulfonium Bromide Catalyzed Synthesis of Pyrazole-Fused Isocoumarins

  • Fang Zhixing ,
  • Liu Juyan ,
  • Qiao Yanhong
Expand
  • 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 date: 2018-03-14

  Revised date: 2018-05-05

  Online published: 2018-05-24

Supported by

Project supported by the Natural Science Foundation of Tianjin City (No. 12JCZDJC34300), and the College Students' Entrepreneurship Training Program (No. 201447).

摘要

在溴化二甲基溴化硫(BDMS)催化作用下,以水合茚三酮和芳腙为原料,在室温下,合成了一系列吡唑稠合型异香豆素衍生物.该合成方法具有反应条件温和、操作简单、催化剂易得、反应时间短的优点.

本文引用格式

房智兴 , 刘巨艳 , 乔艳红 . 溴化二甲基溴化硫催化下吡唑稠合型异香豆素的合成[J]. 有机化学, 2018 , 38(8) : 1985 -1992 . DOI: 10.6023/cjoc201803019

Abstract

A series of pyrazole-fused isocoumarins were synthesized by the reaction of ninhydrin hydrate and arylhydrazones in the presence of bromodimethylsulfonium bromide (BDMS) at room temperature. The reaction has the advantages of mild conditions, simple operation, the ready accessibility of the catalyst, and short reaction times.

参考文献

[1] (a) Barry, R. D. Chem. Rev. 1964, 64, 229.
(b) Hill, R. A. Progress in the Chemistry of Organic Natural Products, Springer, Berlin, 1986; Vol. 49, p. 1.
[2] (a) Engelmeier, D.; Hadacek, F.; Hofer, O.; Lutz-Kutschera, G.; Nagl, M.; Wurz, G.; Greger, H. J. Nat. Prod. 2004, 67, 19.
(b) Rukachaisirikul, V.; Rodglin, A.; Sukpondma, Y.; Phongpaichit, S.; Buatong, J.; Sakayaroj, J. J. Nat. Prod. 2012, 75, 853.
[3] (a) Yoshikawa, M.; Harada, E.; Naitoh, Y.; Inoue, K.; Matsuda, H.; Shimoda, H.; Yamahara, J.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 2225.
(b) Kornsakulkarn, J.; Thongpanchang, C.; Lapanun, S.; Srichom-thong, K. J. Nat. Prod. 2009, 72, 1341.
[4] (a) Kawano, T.; Agata, N.; Kharbanda, S.; Avigan, D.; Kufe, D. Cancer Chemother. Pharmacol. 2007, 59, 329.
(b) Riveiro, M. E.; Moglioni, A.; Vazquez, R.; Gomez, N.; Facorro, G.; Piehl, L.; DeCelis, E. R.; Shayo, C.; Davio, C. Bioorg. Med. Chem. 2008, 16, 2665.
[5] Yoshikawa, M.; Harada, E.; Naitoh, Y.; Inoue, K.; Matsuda, H.; Shimoda, H.; Yamahara, J.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 2225.
[6] Furuta, T.; Fukuyama, Y.; Asakawa, Y. Phytochemistry 1986, 25, 517.
[7] (a) Shikishima, Y.; Takaishi, Y.; Honda, G.; Ito, M.; Takeda, Y.; Kodzhimatov, O. K.; Ashurmetov, O.; Lee, K. H. Chem. Pharm. Bull. 2001, 49, 877.
(b) Goldman, M. E.; Salituro, G. S.; Bowen, J. A.; Williamson, J. M.; Zink, L.; Schleif, W. A.; Emini, E. A. Mol. Pharmacol. 1990, 38, 20.
[8] Gage, B. F. Hematology 2006, 2006, 467
[9] (a) Kurume, A.; Kamata, Y.; Yamashita, M.; Wang, Q.; Matsuda, H.; Yoshikawa, M.; Kawasaki, I.; Ohta, S. Chem. Pharm. Bull. 2008, 56, 1264.
(b) Matsuda, H.; Wang, Q.; Matsuhira, K.; Nakamura, S.; Yuan, D.; Yoshikawa, M. Phytomedicine 2008, 15, 177.
(c) Yoshikawa, M.; Harada, E.; Naitoh, Y.; Inoue, K.; Matsuda, H.; Shimoda, H.; Yamahara, J.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 2225.
[10] Lim, D.-S.; Kwak, Y.-S.; Kim, J.-H.; Ko, S.-H.; Yoon, W.-H.; Kim, C.-H. Chemotherapy. 2003, 49, 146.
[11] (a) Kawano, T.; Agata, N.; Kharbanda, S.; Avigan, D.; Kufe, D. Cancer Chemother. Pharmacol. 2007, 59, 329.
(b) Agata, N.; Nogi, H.; Milhollen, M.; Kharbanda, S.; Kufe, D. Cancer Res. 2004, 64,, 8512.
[12] Maggio, B.; Raffa, D.; Raimondi, M. V.; Plescia, F.; Trincavelli, M. L.; Martini, C.; Meneghetti, F.; Basile, L.; Guccione, S.; Daidone, G. Eur. J. Med. Chem. 2012, 54, 709.
[13] Angelis, M. D.; Stossi, F.; Waibel, M.; Katznellenbogen, B. S.; Katznellenbogen, J. S. Bioorg. Med. Chem. 2005, 13, 6529.
[14] Maggio, B.; Raffa, D.; Raimondi, M. V.; Plescia, F.; Trincavelli, M. L.; Martini, C.; Meneghetti, F.; Basile, L.; Guccione, S.; Daidone, G. Eur. J. Med. Chem. 2012, 54, 709.
[15] (a) Kavala, V.; Wang, C.-C.; Barange, D. K.; Kuo, C.-W.; Lei, P.-M.; Yao, C.-F. J. Org. Chem. 2012, 77, 5022.
(b) Chary, R. G.; Reddy, G. R.; Ganesh, Y. S. S.; Prasad, K. V.; Chandra, S. K. P.; Mukherjee, S.; Pal, M. RSC Adv. 2013, 3, 9641.
(c) Suzuki, T.; Yamada, T.; Watanabe, K.; Katoh, T. Bioorg. Med. Chem. Lett. 2005, 15, 2583.
(d) Deponti, M.; Kozhushkov, S. I.; Yufit, D. S.; Ackermann, L. Org. Biomol. Chem. 2013, 11, 142.
(e) Li, Z.; Hong, J.; Weng, L.; Zhou, X. Tetrahedron 2012, 68, 1552.
[16] (a) Hellal, M.; Bourguignon, J. J.; Bihel, F. J.-J. Tetrahedron Lett. 2008, 49, 62.
(b) da Penha, E. T.; Forni, J. A.; Biajoli, A. F. P.; Correia, C. R. D. Tetrahedron Lett. 2011, 52, 6342.
(c) Kraus, G. A.; Ridgeway, J. J. Org. Chem. 1994, 59, 4735.
[17] Mukherjee, S,; Kundu, A.; Pramanik, A. Tetrahedron Lett. 2016, 57, 2103.
[18] Yadav, V. B.; Rai, P.; Sagir, H.; Kumar, A.; Siddiqui, I. R. ChemistrySelect 2017, 2, 8320.
[19] (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, 212.
[20] (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.
[21] (a) Zhao, C. Y.; Liu, J. Y.; Wang, Y.; Zhao, X. J.; Yuan, B.; Yue, M. M. Synth. Commun. 2014, 44, 827.
(b) Yue, M. M.; Liu, J. Y.; Wang, Y.; Yuan, B. Chin. J. Org. Chem. 2014, 34, 190(in Chinese). (岳闽敏, 刘巨艳, 王英, 袁斌, 有机化学, 2014, 34, 190.)
(c) Zhang, L. J.; Liu, J. Y.; Wang, Y. Chin. J. Org. Chem. 2013, 33, 339(in Chinese). (张丽君, 刘巨艳, 王英, 有机化学, 2013, 33, 339.)
(d) Huang, H. J.; Liu, J. Y.; Ma, E. Z.; Cao, Y. Y. Chin. J. Org. Chem. 2015, 35, 2372(in Chinese). (黄海静, 刘巨艳, 马恩忠, 曹映玉, 有机化学, 2015, 35, 2372.)
(e) Liu, J. Y.; Huang, H. J.; Jiao, D. Q. Chin. J. Org. Chem. 2017, 37, 1808(in Chinese). (刘巨艳, 黄海静, 焦德全, 有机化学, 2017, 37, 1808.)
[22] Nagalakshmi, G..; Maity, T. K.; Maiti, B. C. Pharmacologyonline 2011, 1, 1228.
[23] Dikusar, E. A.; Potkin, V. I. Russ. J. Gen. Chem. 2009, 79, 953.
[24] Majed, M. H. Eur. J. Chem. 2009, 6, 508.

文章导航

/