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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 10: 3452 - 3462

DOI: https://doi.org/10.6023/cjoc202003005

Enantioselective Synthesis of Triarylmethanes Bearing Pyrazole Moiety through Squaramide-Catalyzed Addition of Azadienes with Pyrazolin-5-ones

  • Xie Huanping ,
  • Wu Bo ,
  • Chen Muwang ,
  • Yu Changbin ,
  • Li Hongwang ,
  • Li Xiang ,
  • Zhou Yonggui
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  • a Zhang Dayu School of Chemistry, Dalian University of Technology, Dalian 116024;
    b State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023

Received date: 2020-03-03

  Revised date: 2020-03-27

  Online published: 2020-04-13

Supported by

Project supported by the National Natural Science Foundation of China (No. 21690074).

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Abstract

Using cinchona-derived bifunctional squaramides as catalyst, an asymmetric addition of aurone-derived azadienes with pyrazolin-5-ones was developed, providing a series of chiral triarylmethanes bearing pyrazole moiety with up to 99% ee.

Key words： triarylmethane; pyrazole; organocatalysis; azadiene; enantioselective addition

Cite this article

Xie Huanping , Wu Bo , Chen Muwang , Yu Changbin , Li Hongwang , Li Xiang , Zhou Yonggui . Enantioselective Synthesis of Triarylmethanes Bearing Pyrazole Moiety through Squaramide-Catalyzed Addition of Azadienes with Pyrazolin-5-ones[J]. Chinese Journal of Organic Chemistry, 2020 , 40(10) : 3452 -3462 . DOI: 10.6023/cjoc202003005

References

[1] (a) Finocchiaro, P.; Gust, D.; Mislow, K. J. Am. Chem. Soc. 1974, 96, 3198.
(b) Dothager, R. S.; Putt, K. S.; Allen, B. J.; Leslie, B. J.; Nesterenko, V.; Hergenrother, P. J. J. Am. Chem. Soc. 2005, 127, 8686.
(c) Palchaudhuri, R.; Nesterenko, V.; Hergenrother, P. J. J. Am. Chem. Soc. 2008, 130, 10274.
(d) Gemma, S.; Campiani, G.; Butini, S.; Kukreja, G.; Joshi, B. P.; Persico, M.; Catalanotti, B.; Novellino, E.; Fattorusso, E.; Nacci, V.; Savini, L.; Taramelli, D.; Basilico, N.; Morace, G.; Yardley, V.; Fattorusso, C. J. Med. Chem. 2007, 50, 595.
(e) Snyder, S. A.; Breazzano, S. P.; Ross, A. G.; Lin, Y.; Zografos, A. L. J. Am. Chem. Soc. 2009, 131, 1753.
(f) Mibu, N.; Yokomizo, K.; Uyeda, M.; Sumoto, K. Chem. Pharm. Bull. 2005, 53, 1171.
(g) Mibu, N.; Yokomizo, K.; Miyata, T.; Sumoto, K. J. Heterocycl. Chem. 2010, 47, 1434.
(h) Panda, G.; Shagufta; Mishra, J. K.; Chaturvedi, V.; Srivastava, A. K.; Srivastava, R.; Srivastava, B. S. Bioorg. Med. Chem. 2004, 12, 5269.
(i) Panda, G.; Shagufta; Srivastava, A. K.; Sinha, S. Bioorg. Med. Chem. Lett. 2005, 15, 5222.
(j) Kashyap, V. K.; Gupta, R. K.; Shrivastava, R.; Srivastava, B. S.; Srivastava, R.; Parai, M. K.; Singh, P.; Bera, S.; Panda, G. J. Antimicrob. Chemother. 2012, 67, 1188.
[2] For reviews of triarylmethanes and hetero-triarylmethanes, see: (a) Duxbury, D. F. Chem. Rev. 1993, 93, 381.
(b) Mondal, S.; Panda, G. RSC Adv. 2014, 4, 28317.
(c) Mondal, S.; Roy, D.; Panda, G. ChemCatChem 2018, 10, 1941.
[3] For selected examples of bioactive hetero-triarylmethanes:(a) Whitesitt, C. A.; Whitehead, C. W. J. Med. Chem. 1974, 17, 1298.
(b) Parai, M. K.; Panda, G.; Chaturvedi, V.; Manju, Y. K.; Sinha, S. Bioorg. Med. Chem. Lett. 2008, 18, 289.
(c) Yin, L.; Hu, Q.; Hartmann, R. W. J. Med. Chem. 2013, 56, 460.
[4] Selected examples of bioactive pyrazoles:(a) Fujimori, Y.; Katsuno, K.; Nakashima, I.; Ishikawa-Takemura, Y.; Fujikura, H.; Isaji, M. J. Pharmacol. Exp. Ther. 2008, 327, 268.
(b) Enders, D.; Grossmann, A.; Gieraths, B.; Düzdemir, M.; Merkens, C. Org. Lett. 2012, 14, 4254.
(c) Hack, D.; Chauhan, P.; Deckers, K.; Mizutani, Y.; Raabea, G.; Enders, D. Chem. Commun. 2015, 51, 2266.
(d) Prasanna, S.; Manivannan, E.; Chaturvedi, S. C. Bioorg. Med. Chem. Lett. 2005, 15, 2097.
[5] (a) Chauhan, P.; Mahajan S.; Enders, D. Chem. Commun. 2015, 51, 12890.
(b) Luo, L.; Cao, X.-M.; Lai, G.-W.; Liu, J.-X.; Luo, H.-Q.; Lu, D.-L.; Zhang, Y. Chin. J. Org. Chem. 2020, 40, 1323(in Chinese). (罗亮, 曹晓梅, 赖国伟, 刘金香, 罗海清, 路东亮, 张勇, 有机化学, 2020, 40, 1323.)
(c) Wang, S.; Zhang, B.; Chen, J.; Zheng, Y.; Feng, N.; Ma, A.; Xu, X.; Abdullah, M. A. Chin. J. Org. Chem. 2020, 40, 15(in Chinese). (王少华, 张帮红, 陈洁, 郑莹莹, 冯娜, 马爱军, 徐学涛, Abdullah M. Asiri, 有机化学, 2020, 40, 15.)
[6] Yetra, S. R.; Mondal, S.; Suresh, E.; Biju, A. T. Org. Lett. 2015, 17, 1417.
[7] (a) Vetica, F.; Bailey, S.; Chauhan, P.; Turberg, M.; Ghaur, A.; Raabe, G.; Enders, D. Adv. Synth. Catal. 2017, 359, 3729.
(b) Bao, X.; Wei, S.; Qu, J.; Wang, B. Chem. Commun. 2018, 54, 2028.
(c) Sharma, V.; Kaur, A.; Sahoo, S. C.; Chimni, S. S. Org. Biomol. Chem. 2018, 16, 6470.
[8] (a) Kumarswamyreddy, N.; Kesavan, V. Org. Lett. 2016, 18, 1354.
(b) Luo, W.; Song, D.; Fang, L.; Nian, S.; Hou, H.; Ling, F.; Zhong, W. Asian J. Org. Chem. 2018, 7, 2417.
(c) Sharma, A.; Sharma, V.; Chimni, S. S. Org. Biomol. Chem. 2019, 17, 9514.
[9] (a) Gogoi, S.; Zhao, C.-G. Tetrahedron Lett. 2009, 50, 2252.
(b) Xie, J.; Xing, X.-Y.; Sha, F.; Wu, Z.-Y.; Wu, X.-Y. Org. Biomol. Chem. 2016, 14, 8346.
[10] (a) Liao, Y.-H.; Chen, W.-B.; Wu, Z.-J.; Du, X.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Adv. Synth. Catal. 2010, 352, 827.
(b) Li, F.; Sun, L.; Teng, Y.; Yu, P.; Zhao, J. C.-G.; Ma, J.-A. Chem.- Eur. J. 2012, 18, 14255.
(c) Li, J.-H.; Du, D.-M. Org. Biomol. Chem. 2015, 13, 5636.
(d) Hack, D.; Chauhan, P.; Deckers, K.; Mizutani, Y.; Raabea, G.; Enders, D. Chem. Commun. 2015, 51, 2266.
(e) Amireddy, M.; Chen, K. RSC Adv. 2016, 6, 77474.
(f) Zheng, Y.; Cui, L.; Wang, Y.; Zhou, Z. J. Org. Chem. 2016, 81, 4340.
(g) Li, J.-H.; Cui, Z.-H.; Du, D.-M. Org. Chem. Front. 2016, 3, 1087.
(h) Hack, D.; Dürr, A. B.; Deckers, K.; Chauhan, P.; Seling, N.; Rübenach, L.; Mertens, L.; Raabe, G.; Schoenebeck, F.; Enders, D. Angew. Chem., Int. Ed. 2016, 55, 1797.
(i) Sharma, V.; Kaur, J.; Chimni, S. S. Eur. J. Org. Chem. 2018, 3489.
(j) Phelan, J. P.; Ellman, J. A. Adv. Synth. Catal. 2016, 358, 1713.
(k) Li, F.; Pei, W.; Wang, J.; Liu, J.; Wang, J.; Zhang, M.-L.; Chen, Z.; Liu, L. Org. Chem. Front. 2018, 5, 1342.
(l) Vila, C.; Slack, S.; Blay, G.; Muñoz, M. C.; Pedro, J. R. Adv. Synth. Catal. 2019, 361, 1902.
(m) Rao, K. S.; Ramesh, P.; Trivedi, R.; Kantam, M. L. Tetrahedron Lett. 2016, 57, 1227.
[11] (a) Bao, X.; Wang, B.; Cui, L.; Zhu, G.; He, Y.; Qu, J.; Song, Y. Org. Lett. 2015, 17, 5168.
(b) Amr, F. I.; Vila, C.; Blay, G.; Muñoz, M. C.; Pedro, J. R. Adv. Synth. Catal. 2016, 358, 1583.
(c) Vila, C.; Amr, F. I.; Blay, G.; Muñoz, M. C.; Pedro, J. R. Chem.- Asian J. 2016, 11, 1532.
[12] Yuan, H.; Li, Y.; Zhao, H.; Yang, Z.; Li, X.; Li, W. Chem. Commun. 2019, 55, 12715.
[13] Zhou, J.; Huang, W.-J.; Jiang, G.-F. Org. Lett. 2018, 20, 1158.
[14] (a) Yang, L.-C.; Rong, Z.-Q.; Wang, Y.-N.; Tan, Z. Y.; Wang, M.; Zhao, Y. Angew. Chem., Int. Ed. 2017, 56, 2927.
(b) Rong, Z.-Q.; Yang, L.-C.; Liu, S.; Yu, Z.; Wang, Y.-N.; Tan, Z. Y.; Huang, R.-Z.; Lan, Y.; Zhao, Y. J. Am. Chem. Soc. 2017, 139, 15304.
(c) Wang, Y.-N.; Yang, L.-C.; Rong, Z.-Q.; Liu, T.-L.; Liu, R.; Zhao, Y. Angew. Chem., Int. Ed. 2018, 57, 1596.
(d) Qi, J.; Tang, H.; Chen, C.; Cui, S.; Xu, G. Org. Chem. Front. 2019, 6, 2760.
(e) Liu, Y.-Z.; Wang, Z.; Huang, Z.; Zheng, X.; Yang, W.-L.; Deng, W.-P. Angew. Chem., Int. Ed. 2020, 59, 1238.
(f) Xie, H.-P.; Sun, L.; Wu, B.; Zhou, Y.-G. J. Org. Chem. 2019, 84, 15498.
(g) Kuamri, P.; Liu, W.; Wang, C.-J.; Dai, J.; Wang, M.-X.; Yang, Q.-Q.; Deng, Y.-H.; Shao, Z.-H. Chin. J. Chem. 2020, 38, 511.
(h) Trost, B. M.; Zuo, Z. Angew. Chem., Int. Ed. 2020, 59, 1243.
[15] (a) Rong, Z.-Q.; Wang, M.; Chow, C. H. E.; Zhao, Y. Chem.-Eur. J. 2016, 22, 9483.
(b) Ni, H.; Tang, X.; Yao, W.; Ullah, N.; Lu, Y. Angew. Chem., Int. Ed. 2017, 56, 14222.
(c) Chen, J.; Huang, Y. Org. Lett. 2017, 19, 5609.
[16] (a) Gao, Z.-H.; Chen, K.-Q.; Zhang, Y.; Kong, L.-M.; Li, Y.; Ye, S. J. Org. Chem. 2018, 83, 15225.
(b) Chen, K.-Q.; Gao, Z.-H.; Ye, S. Org. Chem. Front. 2019, 6, 405.
[17] Xie, H.-P.; Wu, B.; Wang, X.-W.; Zhou, Y.-G. Chin. J. Catal. 2019, 40, 1566.
[18] (a) Chen, J.; Jia, P.; Huang, Y. Org. Lett. 2018, 20, 6715.
(b) Zeng, R.; Shan, C.; Liu, M.; Jiang, K.; Ye, Y.; Liu, T.-Y.; Chen, Y.-C. Org. Lett. 2019, 21, 2312.
(c) Marques, A.-S.; Duhail, T.; Marrot, J.; Chataigner, I.; Coeffard, V.; Vincent, G.; Moreau, X. Angew. Chem., Int. Ed. 2019, 58, 9969.
[19] (a) Gu, Z.; Zhou, J.; Jiang, G.-F.; Zhou, Y.-G. Org. Chem. Front. 2018, 5, 1148.
(b) Gu, Z.; Xie, J.-J.; Jiang, G.-F.; Zhou, Y.-G. Asian J. Org. Chem. 2018, 7, 1561.
(c) Lin, W.; Zhang, C.; Xu, W.; Cheng, Y.; Li, P.; Li, W. Adv. Synth. Catal. 2019, 361, 476.
(d) Lin, W.; Lin, X.; Cheng, Y.; Chang, X.; Zhou, S.; Li, P.; Li, W. Org. Chem. Front. 2019, 6, 2452.
(e) Gu, Z.; Wu, B.; Jiang, G.-F.; Zhou, Y.-G. Chin. J. Chem. 2018, 36, 1130.
(f) Wang, C.-S.; Li, T.-Z.; Cheng, Y.-C.; Zhou, J.; Mei, G.-J.; Shi, F. J. Org. Chem. 2019, 84, 3214.
(g) Li, X.; Yan, J.; Qin, J.; Lin, S.; Chen, W.; Zhan, R.; Huang, H. J. Org. Chem. 2019, 84, 8035.
(h) Fan, T.; Zhang, Z.-J.; Zhang, Y.-C.; Song, J. Org. Lett. 2019, 21, 7897.
(i) Wang, C.-J.; Yang, Q.-Q.; Wang, M.-X.; Shang, Y.-H.; Tong, X.-Y.; Deng, Y.-H.; Shao, Z. Org. Chem. Front. 2020, 7, 609.
[20] Yan, Z.; Gao, X.; Zhou, Y.-G. Chin. J. Catal. 2017, 38, 784.
[21] Löser, R.; Chlupacova, M.; Marecek, A.; Opletalova, V.; Gütschow, M. Helv. Chim. Acta 2004, 87, 2597.
[22] (a) Ouellet, S. G.; Gauvreau, D.; Cameron, M.; Dolman, S.; Campeau, L.-C.; Hughes, G.; O'Shea, P. D.; Davies, I. W. Org. Process Res. Dev. 2012, 16, 214.
(b) Tsou, H.-R.; MacEwan, G.; Birnberg, G.; Zhang, N.; Brooijmans, N.; Barza, L. T.; Hollander, I.; Kaloustian, S. A.; Yu, K. Bioorg. Med. Chem. Lett. 2010, 20, 2259.
[23] (a) Wang, X.-J.; Tan, J.; Grozinger, K. Tetrahedron Lett. 2000, 41, 4713.
(b) Braňa, M. F.; Gradillas, A.; Ovalles, A. G.; López, B.; Acero, N.; Llinares, F.; Mingarro, D. M. Bioorg. Med. Chem. 2006, 14, 9.
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