Chinese Journal of Organic Chemistry >
Bromodimethylsulfonium Bromide Catalyzed Synthesis of Pyrazole-Fused Isocoumarins
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).
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.
Key words: ninhydrin hydrate; arylhydrazones; pyrazole-fused isocoumarins; BDMS
Fang Zhixing , Liu Juyan , Qiao Yanhong . Bromodimethylsulfonium Bromide Catalyzed Synthesis of Pyrazole-Fused Isocoumarins[J]. Chinese Journal of Organic Chemistry, 2018 , 38(8) : 1985 -1992 . DOI: 10.6023/cjoc201803019
[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.
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