Citation: 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 shu

Bromodimethylsulfonium Bromide Catalyzed Synthesis of Pyrazole-Fused Isocoumarins

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

Corresponding author: Liu Juyan, hxxyljy@mail.tjnu.edu.cn
Received Date: 14 March 2018
Revised Date: 5 May 2018
Available Online: 24 August 2018
Fund Project: the Natural Science Foundation of Tianjin City 12JCZDJC34300Project supported by the Natural Science Foundation of Tianjin City (No. 12JCZDJC34300), and the College Students' Entrepreneurship Training Program (No. 201447)the College Students' Entrepreneurship Training Program 201447

Figures(2)

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.
- ninhydrin hydrate,
- arylhydrazones,
- pyrazole-fused isocoumarins,
- BDMS
1. [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. [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. [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. [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. [5]
  Yoshikawa, M.; Harada, E.; Naitoh, Y.; Inoue, K.; Matsuda, H.; Shimoda, H.; Yamahara, J.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 2225. doi: 10.1248/cpb.42.2225
6. [6]
  Furuta, T.; Fukuyama, Y.; Asakawa, Y. Phytochemistry 1986, 25, 517. doi: 10.1016/S0031-9422(00)85513-2
7. [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. [8]
  Gage, B. F. Hematology 2006. 2006, 467 doi: 10.1182/asheducation-2006.1.467
9. [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. [10]
  Lim, D.-S.; Kwak, Y.-S.; Kim, J.-H.; Ko, S.-H.; Yoon, W.-H.; Kim, C.-H. Chemotherapy. 2003, 49, 146. doi: 10.1159/000070621
11. [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. [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. doi: 10.1016/j.ejmech.2012.06.028
13. [13]
  Angelis, M. D.; Stossi, F.; Waibel, M.; Katznellenbogen, B. S.; Katznellenbogen, J. S. Bioorg. Med. Chem. 2005, 13, 6529. doi: 10.1016/j.bmc.2005.07.014
14. [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. doi: 10.1016/j.ejmech.2012.06.028
15. [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. [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. [17]
  Mukherjee, S, ; Kundu, A.; Pramanik, A. Tetrahedron Lett. 2016, 57, 2103. doi: 10.1016/j.tetlet.2016.04.002
18. [18]
  Yadav, V. B.; Rai, P.; Sagir, H.; Kumar, A.; Siddiqui, I. R. ChemistrySelect 2017, 2, 8320. doi: 10.1002/slct.201700976
19. [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. [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. [21]
22. [22]
  Nagalakshmi, G..; Maity, T. K.; Maiti, B. C. Pharmacologyonline 2011, 1, 1228.
23. [23]
  Dikusar, E. A.; Potkin, V. I. Russ. J. Gen. Chem. 2009, 79, 953. doi: 10.1134/S1070363209050144
24. [24]
  Majed, M. H. Eur. J. Chem. 2009, 6, 508.
1. [1]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
2. [2]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
3. [3]
  Chunyan Hu , Wei Wang , Zewei Mao , Mei Zhang , Lei Zhang , Yuping Lin . Three-stage progressive teaching reform and practice in organic chemistry experiments for pharmacy undergraduates: synthesis of coumarin-chalcone derivatives. University Chemistry, 2026, 41(7): 282-289. doi: 10.12461/PKU.DXHX202505011
4. [4]
  Jianding LI , Junyang FENG , Huimin REN , Gang LI . Proton conductive properties of a Hf(Ⅳ)-based metal-organic framework built by 2,5-dibromophenyl-4,6-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1094-1100. doi: 10.11862/CJIC.20240464
5. [5]
  Junyang FENG , Xiaoli HAN , Yongjie SONG , Gang LI . Proton conduction and fluorescence properties of an ionic hydrogen-bonded organic framework constructed from dibromophthalic acid. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 693-702. doi: 10.11862/CJIC.20250350
6. [6]
  Botao QU , Qian WANG , Qian WANG , Ruiping ZHANG . Synthesis, crystal structures, and luminescence properties of zinc coordination polymers based on 2,5-dibromoterephthalate. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 917-924. doi: 10.11862/CJIC.20260357
7. [7]
  Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
8. [8]
  Ranhui Fu , Shixin Zhou , Ran Ji , Feifei Gao , Hui Xu . 季膦盐合成实验的改进与拓展——水相一步法合成乙基三苯基溴化膦及其力致发光锰配合物的制备及表征. University Chemistry, 2026, 41(5): 252-263. doi: 10.12461/PKU.DXHX202510018
9. [9]
  Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064
10. [10]
  Zhiqiang Hao , Jinyue Li , Shiqi Zhang , Yujia Hou , Helue Sun . 维生素B₂促进的光催化氧化合成二苯甲酮. University Chemistry, 2026, 41(5): 350-357. doi: 10.12461/PKU.DXHX202510080
11. [11]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
12. [12]
  Xing Yan , Yetai Cheng , Yixun Shu , Luyao Yang , Weidong Wang , Xinlu Bai , Ya-Nan Chen , Hao Lu , Zhishan Bo , Yahui Liu . Highly efficient and stable organic solar cells based on dimeric non-fused ring acceptors as the third component. Acta Physico-Chimica Sinica, 2026, 42(7): 100228-0. doi: 10.1016/j.actphy.2025.100228
13. [13]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
14. [14]
  Jinghua Wang , Yanxin Yu , Yanbiao Ren , Yesheng Wang . Integration of Science and Education: Investigation of Tributyl Citrate Synthesis under the Promotion of Hydrate Molten Salts for Research and Innovation Training. University Chemistry, 2024, 39(11): 232-240. doi: 10.3866/PKU.DXHX202402057
15. [15]
  Weifeng HUANG , Jingteng FENG , Xin WANG , Zhilong XU , Jiaxin LI , Guanghui SUN , Yan SUN , Yao SUN , Xi LIU , Yinfeng CHENG , Guangri XU , Li YANG . In-situ self-assembly of hydrated vanadium pentoxide on Zn foil for stable Zn anodes. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 562-570. doi: 10.11862/CJIC.20250267
16. [16]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
17. [17]
  Hua Zhou , Yuqing Li , Rui Zhang , Jialong Qian , Zhenhua Li , Mingfei Shao . 电解水制氢耦合5-羟甲基糠醛氧化制2,5-呋喃二甲酸创新实验设计. University Chemistry, 2026, 41(8): 321-330. doi: 10.12461/PKU.DXHX202507123
18. [18]
  Fengcheng Jia , Zixia Zheng , Fei Li , Huiqin Duan , Gang Wang . 串联S_NAr/Aldol缩合构建季碳稠合吲哚啉. University Chemistry, 2026, 41(5): 190-197. doi: 10.12461/PKU.DXHX202511104
19. [19]
  Shiyi Chen , Jialong Fu , Jianping Qiu , Guoju Chang , Shiyou Hao . Waste medical mask-derived carbon quantum dots enhance the photocatalytic degradation of polyethylene terephthalate (PET) over BiOBr/g-C₃N₄ S-scheme heterojunction. Acta Physico-Chimica Sinica, 2026, 42(1): 100135-0. doi: 10.1016/j.actphy.2025.100135
20. [20]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(1848)
HTML views(167)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142