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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 4: 1068 - 1073

DOI: https://doi.org/10.6023/cjoc201908031

I2/CuO-Catalyzed One-Pot Synthesis of 3-(2-Amino-4-thiazolyl) Coumarin Derivatives from 3-Acetylcoumarins and Thiourea

  • Zhao Fang ,
  • Hu Yang ,
  • Li Qiao ,
  • Hu Shengli
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  • College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi 435002

Received date: 2019-08-23

  Revised date: 2019-10-19

  Online published: 2019-11-07

Supported by

Project supported by the Science Technology Foundation for Creative Research Group of Hubei Department of Education (No. T201311) and the Foundation of Hubei Provincal Ministry of Education (No. D20112507).

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Abstract

Coumarin and thiazole are two classes of important heterocycles with many biological activities and pharmacological effects. It is very meaningful to synthesize thiazolyl coumarin derivatives in medicinal chemistry area. In this study, a facile and efficient one-pot process was developed to synthesize substituted aminothiazoles from 3-acetylcoumarins and thiourea/N-substituted thioureas under the media of I2/CuO. All target molecules were characterized by NMR, IR spectra and MS.

Key words： coumarin; 2-aminothiazole; one-pot reaction; I2/CuO

Cite this article

Zhao Fang , Hu Yang , Li Qiao , Hu Shengli . I2/CuO-Catalyzed One-Pot Synthesis of 3-(2-Amino-4-thiazolyl) Coumarin Derivatives from 3-Acetylcoumarins and Thiourea[J]. Chinese Journal of Organic Chemistry, 2020 , 40(4) : 1068 -1073 . DOI: 10.6023/cjoc201908031

References

[1] Spino, C.; Dodier, M. Sotheeswaran, S. Bioorg. Med. Chem. Lett. 1998, 8, 3475.
[2] Witaicenis, A.; Seito, L. N.; Di Stasi, L. C. Chem. Biol. Interact. 2010, 186, 211.
[3] Arora, R. K.; Kaur, N.; Bansal, Y.; Bansal, G. Acta Pharm. Sin. B 2014, 4, 368.
[4] Basile, A.; Sorbo, S.; Spadaro, V. Molecules 2009, 14, 939.
[5] Huang, X.; Liu, J. Chin. J. Org. Chem. 2018, 38, 1233(in Chinese). (黄新炜, 刘建利, 有机化学, 2018, 38, 1233.)
[6] Sun, H.; Sun, H.; Liu, M.; Huang, W.; Yang, G. Chin. J. Org. Chem. 2018, 38, 2067(in Chinese). (孙海燕, 孙宏顺, 刘明珍, 黄伟, 杨光富, 有机化学, 2018, 38, 2067.)
[7] Fang, Z. X.; Liu, J. Y.; Qiao, Y. H. Chin. J. Org. Chem. 2018, 38, 1985(in Chinese). (房智兴, 刘巨艳, 乔艳红, 有机化学, 2018, 38, 1985.)
[8] Kim, J.; Moon, Y.; Ham, S. W. Bull. Korean Chem. Soc. 2011, 32, 2893.
[9] Ding, C.; Pan, Y.; Yin, X.; Tan, C. Chin. J. Org. Chem. 2019, 39, 2099(in Chinese). (丁成荣, 潘亚运, 殷许, 谭成侠, 有机化学, 2019, 39, 2099.)
[10] Xu, J.; Ma, L.; Liu, X. B. Chin. J. Org. Chem. 2018, 38, 1680(in Chinese). (徐姣, 马玲, 刘秀波, 有机化学, 2018, 38, 1680.)
[11] Zhang, Q.; Wang, Y.; Zhao, Y.; Ma, C.; Xu, X.; Gu, W.; Yang, Y.; Wang, S. Chin. J. Org. Chem. 2019, 39, 2616(in Chinese). (张强健, 王芸芸, 赵雨珣, 马崇慧, 徐徐, 谷文, 杨益琴, 王石发, 有机化学, 2019, 39, 2616.)
[12] Koelsch, C. F. J. Am. Chem. Soc. 1950, 72, 2993.
[13] Vardhan, V. A.; Rao, V. R. Indian J. Chem., Sect. B 1997, 36, 1085.
[14] Ramanna, S.; Rao, V. R.; Kumari, T. S.; Rao, T. V. P. Phosphorus Sulfur Relat. Elem. 1995, 107, 197.
[15] Czerney, P.; Hartmann, H. J. Prakt. Chem. 1983, 325, 551.
[16] Ramagiri, R. K.; Vedula, R. R.; Thupurani, M. K. Phosphorus sulfur Relat. Elem. 2015, 190, 1393.
[17] Zhuravel, I. O.; Kovalenko, S. M.; Vlasov, S. V.; Chernykh, V. P. Molecules 2005, 10, 444.
[18] Ramesh, G.; Janardhan, B.; Rajitha, B. Res. Chem. Intermed. 2015, 41, 8099.
[19] Chunduru, V. S. R.; Rao, R. V. J. Chem. Res. 2010, 34, 50.
[20] Saeed, A.; Ejaz, S. A.; Shehzad, M.; Hassan, S.; al-Rashida, M.; Lecka, J.; Sévigny, J.; Iqbal, J. RSC Adv. 2016, 6, 21026.
[21] Hande, P. E.; Samui, A. B.; Kulkarni, P. S. Sens. Actuators, B 2017, 246, 597.
[22] Patil, N. T.; Shinde, V. S.; Gajula, B. Org. Biomol. Chem. 2012, 10, 211.
[23] Fan, L.; Yao, C.; Shu, M. Heterocycl. Commun. 2016, 22, 63.
[24] Jadhvar, S. C.; Kasraliker, H. M.; Goswami, S. V.; Chakrawar, A. V.; Bhusare, S. R. Res. Chem. Intermed. 2017, 43, 7211.
[25] Jannati, S.; Esmaeili, A. A. Res. Chem. Intermed. 2017, 43, 6817.
[26] Reddy, K. M. K.; Sadik, S. M.; Saichaithanya, N.; Peddanna, K.; Reddy, N. B.; Sravya, G.; Grigory V, Z.; Reddy, C. S. Res. Chem. Intermed. 2017, 43, 7087.
[27] Kim, K. M.; Ryu, E. K. Tetrahedron Lett. 1996, 37, 1441.
[28] More, S. V.; Sastry, M. N. V.; Wang, C. C.; Yao, C. F. Tetrahedron Lett. 2005, 46, 6345.
[29] Behmadi, H.; Roshani, M.; Saadati, S. M. Chin. Chem. Lett. 2009, 20, 5.
[30] Zhu, Y. P.; Yuan, J. J.; Zhao, Q.; Lian, M.; Gao, Q. H.; Liu, M. C.; Yang, Y.; Wu, A. X. Tetrahedron 2012, 68, 173.
[31] Bogdal, D. J. Chem. Res., Synop. 1998, 468.
[32] Lin, W.; Cao, X.; Yuan, L. Ding, Y. Chem. Eur. J. 2010, 16, 6454.
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