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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 5: 1982 - 1990

DOI: https://doi.org/10.6023/cjoc202012007

ARTICLES

A Rapid Synthesis of 5H-Benzo[d]imidazo[5,1-b][1,3]thiazines via Copper(I)-Catalyzed Cascade Bicyclization ofo-Alkynylphenyl Isothiocyanates with Ethyl (E)-2-(Benzylideneamino)acetates

  • Yahui Zhang ,
  • Wenjin Wu ,
  • Kexin Zhang ,
  • Shuangshuang Li ,
  • Wenyan Hao
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  • 1 Key Laboratory of Functional Small Organic Molecules of Ministry of Education, Jiangxi Key Laboratory of Green Chemistry, College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022
* Corresponding author. E-mail:

Received date: 2020-12-02

  Revised date: 2021-01-18

  Online published: 2021-02-22

Supported by

National Natural Science Foundation of China(21762023); National Natural Science Foundation of China(22061021); Natural Science Foundation of Jiangxi Province(2018BAB203006)

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Abstract

A rapid and efficient protocol for copper(I)-catalyzed tandem bicyclization of o-alkynylphenyl isothiocyanates with ethyl (E)-2-(benzylideneamino)acetates has been developed, affording a series of 5H-benzo[d]imidazo[5,1-b][1,3]thia- zines in moderate to good yields. In this transformation, a [3+2] cycloaddition reaction mechanism was involved and two new rings were formed in one pot.

Key words： Keywords copper-catalysis; cascade bicyclization; 5H-benzo[d]imidazo[5,1-b][1,3]thiazine

Cite this article

Yahui Zhang , Wenjin Wu , Kexin Zhang , Shuangshuang Li , Wenyan Hao . A Rapid Synthesis of 5H-Benzo[d]imidazo[5,1-b][1,3]thiazines via Copper(I)-Catalyzed Cascade Bicyclization ofo-Alkynylphenyl Isothiocyanates with Ethyl (E)-2-(Benzylideneamino)acetates[J]. Chinese Journal of Organic Chemistry, 2021 , 41(5) : 1982 -1990 . DOI: 10.6023/cjoc202012007

References

[1]
Huang, X.; Cong, X.; Mi, P.; Bi, X. Chem. Commun. 2017, 53, 3858.
[2]
(a) Palagiano, F.; Arenare, L.; De Caprariis, P.; Grandolini, G.; Ambrogi, V.; Perioli, L.; Filippelli, W.; Falcone, G.; Rossi, F. Farmaco 1996, 51, 483.
[2]
(b) Shridhar, D. R.; Jogibhukta, M.; Krishnan, V. S. H. Ind. J. Chem. 1982, 21B, 130.
[2]
(c) Raddatz, S.; Bartel, S.; Guarnieri, W.; Rosentreter, U.; Ruppelt, M.; Wild, H.; Endermann, R.; Kroll, H.-P.; Henninger, K. WO 1999/040094, 1999.
[4]
De Peretti, D.; George, P.; Sevrin, M.; Roy, J.; Demande, Fr. FR 2759700, 1998.
[3]
(a) Fryer, R. I.; Lauer, R. F.; Trybulski, E. J.; Vitone, S.; Walser, A.; Zenchoff, G. J. Chem. 1983, 20, 1605.
[3]
(b) Rao, K. V.; Sundaramurthy, V. Sulfur Lett. 1988, 8, 137.
[3]
(c) Rao, K. V.; Sundaramurthy, V. J. Org. Chem. 1992, 57, 2737.
[3]
(d) Petrova, K.; Petrov, O.; Antonova, A.; Kalcheva, V. Heterocycl. Commun. 2003, 9, 593.
[3]
(e) Tu, X.; Li, T.; Zhou, L.; Zhang, Y.; Zeng, Q. Fresenius Environ. Bull. 2013, 22, 3857.
[3]
(f) Omar, M. A.; Conrad, J.; Beifuss, U. Tetrahedron 2014, 70, 5682.
[3]
(g) Tan, F.; Xiao, W. J.; Zeng, G. P. Chin. J. Org. Chem. 2017, 37, 824. (in Chinese).
[3]
(谭芬, 肖文精, 曾国平, 有机化学, 2017, 37, 824.)
[3]
(h) Sun, Y. W.; Zhou, L. Y.; Wang, L. Z. Chin. J. Org. Chem. 2019, 39, 3516. (in Chinese).
[3]
(孙悦玮, 周来运, 王兰芝, 有机化学, 2019, 39, 3516.)
[3]
(i) Yang, W. C.; Zhang, M. M.; Chen, W.; Yang, X. H.; Feng, J. G. Chin. J. Org. Chem. 2020, 40, 4060. (in Chinese).
[3]
(杨文超, 张明明, 陈旺, 杨小虎, 冯建国, 有机化学, 2020, 40, 4060.)
[3]
(j) Sun, X. H.; Sun, C. C.; Feng, L. J.; Kang, C. M. Chin. J. Org. Chem. 2020, 40, 2626. (in Chinese).
[3]
(孙晓华, 孙传策, 冯立军, 康从民, 有机化学, 2020, 40, 2626.)
[4]
Gauthier, J.; Duceppe, J. S. J. Heterocycl. Chem. 1984, 21, 1081.
[5]
Dolbier, W. R.; Burkholder, J. C.; Abboud, K. A.; Loehle, D. J. Org. Chem. 1994, 59, 7688.
[6]
Wang, R. W.; Bao, W. Tetrahedron Lett. 2012, 53, 442.
[7]
(a) Benati, L.; Calestani, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Strazzari, S.; Zanardi, G. J. Org. Chem. 2003, 68, 3454.
[7]
(b) Minozzi, M.; Nanni, D.; Zanardi, G.; Calestani, G. ARKIVOC 2006, 6, 6.
[7]
(c) Saito, T.; Nihei, H.; Otani, T.; Suyama, T.; Furukawa, N.; Saito, M. Chem. Commun. 2008,172.
[7]
(d) Xie, J. L.; Guo, Z. L.; Huang, Y. Q.; Qu, Y.; Song, H. J.; Song, H. B.; Liu, Y. X.; Wang, Q. M. Adv. Synth. Catal. 2019, 361, 490.
[7]
(e) Wen, L.-R.; Shen, Q.-Y.; Guo, W.-S.; Li, M. Org. Chem. Front. 2016, 3, 870.
[8]
(a) Otani, T.; Kunimatsu, S.; Nihei, H.; Abe, Y.; Saito, T. Org. Lett. 2007, 9, 5513.
[8]
(b) Otani, T.; Kunimatsu, S.; Takahashi, T.; Nihei, H.; Saito, T. Tetrahedron Lett. 2009, 50, 3853.
[9]
(a) Kaname, M.; Sashida, H. Tetrahedron Lett. 2012, 53, 748.
[9]
(b) Sashida, H.; Kaname, M.; Minoura, M. Tetrahedron 2013, 69, 6478.
[10]
Liu, R.-J.; Wang, P.-F.; Yuan, W.-K.; Wen, L.-R.; Li, M. Adv. Synth. Catal. 2017, 359, 1373.
[11]
Xie, J. L.; Guo, Z. L.; Huang, Y. Q.; Qu, Y.; Song, H. J.; Song, H. B.; Liu, Y. X.; Wang, Q. M. Adv. Synth. Catal. 2019, 361, 490.
[12]
Miao, J. K.; Zhang, Y. H.; Sang, X. Y.; Hao, W. Y. Org. Biomol. Chem. 2019, 17, 2336.
[13]
(a) Hao, W. Y.; Zeng, J. B.; Cai, M. Z. Chem. Commun. 2014, 50, 11686.
[13]
(b) Hao, W. Y.; Jiang, Y. Y.; Cai, M. Z. J. Org. Chem. 2014, 79, 3634.
[13]
(c) Hao, W. Y.; Huang, J.; Jie, S. S.; Cai, M. Z. Eur. J. Org. Chem. 2015,6655.
[13]
(d) Hao, W. Y.; Sang, X. Y.; Jiang, J.; Cai, M. Z. Tetrahedron Lett. 2016, 57, 1511.
[13]
(e) Hao, W. Y.; Sang, X. Y.; Jiang, J.; Cai, M. Z. Tetrahedron Lett. 2016, 57, 4207.
[13]
(f) Miao, J. K.; Sang, X. Y.; Wang, Y.; Deng, S. F.; Hao, W. Y. Org. Biomol. Chem. 2019, 17, 6994.
[13]
(g) Zhang, Y. H.; Liu, Y.; Miao, J. K.; Hao, W. Y. Chin. J. Org. Chem. 2020, 40, 2426. (in Chinese).
[13]
(张亚辉, 刘洋, 缪建康, 郝文燕, 有机化学, 2020, 40, 2426.)
[13]
(h) Liu, Y.; Yao, S. J.; Wang, C. L.; Zhang, Y. H.; Hao, W. Y. RSC Adv. 2020, 10, 32211.
[14]
(a) Uchiyama, M.; Ozawa, H.; Takuma, K.; Matsumoto, Y.; Yonehara, M.; Hiroya, K.; Sakamoto, T. Org. Lett. 2006, 8, 5517.
[14]
(b) Park, J. H.; Bhilare, S. V.; Youn, S. W. Org. Lett. 2011, 13, 2228.
[14]
(c) Gilmore, K.; Alabugin, I. V. Chem. Rev. 2011, 111, 6513.
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