tBuOK-Promoted Reaction of Selenocyanates and Hydrazones for the Synthesis of Selenoacetals

doi:10.6023/cjoc202106048

Abstract

A series of selenoacetals were synthesized from selenocyanates and hydrazones under base condition. (Hetero)aryl selenocyanate and (hetero)aryl, alkyl hydrazones can undergo the process successfully, and shows broad substrate scope and excellent functional group tolerance. This protocol is suitable for gram-scale preparation, providing an efficient and practical synthetic strategy toward selenoacetals.

Key words: selenocyanate, hydrazone, selenoacetal, rearrangement

Cite this article

Hao Ye, Tingting Ren, Xinxing Wu. ^tBuOK-Promoted Reaction of Selenocyanates and Hydrazones for the Synthesis of Selenoacetals[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4338-4346.

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References 17

[1]	Clive, D. L. J. Tetrahedron 1978, 34, 1049. doi: 10.1016/0040-4020(78)80135-5
[2]	(a) Rao, C. V.; Wang, C.-Q.; Simi, B.; Rodriguez, J. G.; Cooma, I.; El-Bayoumy, K.; Reddy, B. S. Cancer Res. 2001, 61, 3647. pmid: 16620795
	(b) Richie, J. P.; Kleinman, W.; Desai, D. H.; Das, A.; Amin, S. G.; Pinto, J. T.; El-Bayoumy, K. Chem.-Biol. Interact. 2006, 161, 93. pmid: 16620795
	(c) Anan, Y.; Kimura, M.; Hayashi, M.; Koike, R.; Ogra, Y. Chem. Res. Toxicol. 2015, 28, 1803. doi: 10.1021/acs.chemrestox.5b00254 pmid: 16620795
[3]	Dumont, W.; Krief, A. Angew. Chem., nt. Ed. 1977, 16, 540.
[4]	Clive, D. L. J.; Menchen, S. M. J. Org. Chem. 1979, 44, 1883. doi: 10.1021/jo01325a034
[5]	(a) Dong, T.; Nie, J.; Zhang, C. Tetrahedron 2018, 74, 5642. doi: 10.1016/j.tet.2018.08.001 pmid: 11710243
	(b) Yu, Y.; Zhou, Y.; Song, Z.; Liang, G. Org. Biomol. Chem. 2018, 16, 4958. doi: 10.1039/C8OB00948A pmid: 11710243
	(c) Marpna, I. D.; Wanniang, K.; Lipon, T. M.; Risuklang Shangpliang, O.; Myrboh, B. J. Org. Chem. 2021, 86, 1980. doi: 10.1021/acs.joc.0c02630 pmid: 11710243
	(d) Mugesh, G.; Du Mont, W.-W.; Sies, H. Chem. Rev. 2001, 101, 2125. pmid: 11710243
	(e) Wu, Y.; Tian, X.; Zhang, H.; Chen, R.; Cao, T. Chin. J. Org. Chem. 2020, 40, 1384. (in Chinese) doi: 10.6023/cjoc201910003 pmid: 11710243
	(吴燕, 田仙芝, 张海玲, 陈睿, 曹团武, 有机化学, 2020, 40, 1384.) doi: 10.6023/cjoc201910003 pmid: 11710243
[6]	(a) Bürger, M.; Röttger, S. H.; Loch, M. N.; Jones, P. G.; Werz, D. B. Org. Lett. 2020, 22, 5025. doi: 10.1021/acs.orglett.0c01582
	(b) Jacob, A.; Jones, P. G.; Werz, D. B. Org. Lett. 2020, 22, 8720. doi: 10.1021/acs.orglett.0c03329
	(c) Sun, M.; Xu, K.; Guo, B.; Zeng, C. Chin. J. Org. Chem. 2021, 41, 2302. (in Chinese) doi: 10.6023/cjoc202102002
	(孙名扬, 徐坤, 郭兵兵, 曾程初, 有机化学, 2021, 41, 2302.) doi: 10.6023/cjoc202102002
[7]	(a) Maity, P.; Paroi, B.; Ranu, B. C. Org. Lett. 2017, 19, 5748. doi: 10.1021/acs.orglett.7b02571
	(b) Zhu, Y.-S.; Xue, Y.; Liu, W.; Zhu, X.; Hao, X.-Q.; Song, M.-P. J. Org. Chem. 2020, 85, 9106. doi: 10.1021/acs.joc.0c01035
	(c) Wu, D.; Qiu, J.; Li, C.; Yuan, L.; Yin, H.; Chen, F.-X. J. Org. Chem. 2020, 85, 934. doi: 10.1021/acs.joc.9b02786
[8]	(a) Cao, Y.; Jiang, L.; Yi, W. Adv. Synth. Catal. 2019, 361, 4360. doi: 10.1002/adsc.v361.18
	(b) Pan, C.; Liu, P.; Wu, A.; Li, M.; Wen, L.; Guo, W. Chin. J. Org. Chem. 2020, 40, 2855. (in Chinese) doi: 10.6023/cjoc202004051
	(潘超, 刘鹏, 武安国, 李明, 文丽荣, 郭维斯, 有机化学, 2020, 40, 2855.) doi: 10.6023/cjoc202004051
	(c) Krief, A.; Dumont, W.; Delmotte, C. Angew. Chem., nt. Ed. 2000, 39, 1669.
	(d) Wang, J.; Zhou, X.; Fan, W.; Du, S. Acta Chim. Sinica 1992, 50, 504. (in Chinese)
	(王瑾, 周洵钧, 范伟强, 杜少斌, 化学学报, 1992, 50, 504.)
	(e) Zhao, H.-R.; Liu, M.-Q.; Zhao, X.-J. Acta Chim. Sinica 2007, 65, 2155. (in Chinese)
	(赵华绒, 刘曼琼, 赵新建, 化学学报, 2007, 65, 2155.)
	(f) Ge, Y.; Kong, J.; Yang, C.; Yang, Q.; Zhang, X. Chin. J. Org. Chem. 2020, 40, 1760. (in Chinese) doi: 10.6023/cjoc201912022
	(葛颜玉, 孔晶, 杨成根, 杨倩, 张旭, 有机化学, 2020, 40, 1760.) doi: 10.6023/cjoc201912022
[9]	(a) Zhang, Y.; Wang, J. Top. Curr. Chem. 2012, 327, 239. doi: 10.1007/128_2012_322 pmid: 22547357
	(b) Zhu, D.; Chen, L.; Fan, H.; Yao, Q.; Zhu, S. Chem. Soc. Rev. 2020, 49, 908. doi: 10.1039/C9CS00542K pmid: 22547357
	(c) Kaufman, G. M.; Cook, F. B.; Shechter, H.; Bayless, J. H.; Friedman, L. J. Am. Chem. Soc. 1967, 89, 5736. doi: 10.1021/ja00998a061 pmid: 22547357
[10]	(a) Barluenga, J.; Valdes, C. Angew. Chem., nt. Ed. 2011, 50, 7486. pmid: 21378917
	(b) Barluenga, J.; Moriel, P.; Valdes, C.; Aznar, F. Angew. Chem., nt. Ed. 2007, 46, 5587. pmid: 21378917
	(c) Barluenga, J.; Tomas-Gamasa, M.; Aznar, F.; Valdes, C. Nat. Chem. 2009, 1, 494. doi: 10.1038/nchem.328 pmid: 21378917
	(d) Barluenga, J.; Tomas-Gamasa, M.; Aznar, F.; Valdes, C. Angew. Chem., nt. Ed. 2010, 49, 4993. pmid: 21378917
[11]	(a) Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236. doi: 10.1021/ar300101k
	(b) Liu, Z.; Wang, J. J. Org. Chem. 2013, 78, 10024. doi: 10.1021/jo401850q
	(c) Xia, Y.; Zhang, Y.; Wang, J. ACS Catal. 2013, 3, 2586. doi: 10.1021/cs4006666
	(d) Xia, Y.; Qiu, D.; Wang, J. Chem. Rev. 2017, 117, 13810. doi: 10.1021/acs.chemrev.7b00382
	(e) Zhou, Q.; Gao, Y.; Xiao, Y.; Yu, L.; Fu, Z.; Li, Z.; Wang, J. Polym. Chem. 2019, 10, 569. doi: 10.1039/C8PY01529E
	(f) Liu, Z.; Zhang, Y.; Wang, J. Chin. J. Org. Chem. 2013, 33, 687. (in Chinese) doi: 10.6023/cjoc201301023
	(刘振兴, 张艳, 王剑波, 有机化学, 2013, 33, 687.) doi: 10.6023/cjoc201301023
[12]	(a) Chen, Z.-S.; Duan, X.-H.; Wu, L.-Y.; Ali, S.; Ji, K.-G.; Zhou, P.-X.; Liu, X.-Y.; Liang, Y.-M. Chem.-Eur. J. 2011, 17, 6918. doi: 10.1002/chem.201100248
	(b) Wu, X.-X.; Shen, Y.; Chen, W.-L.; Chen, S.; Hao, X.-H.; Xia, Y.; Xu, P.-F.; Liang, Y.-M. Chem. Commun. 2015, 51, 8031. doi: 10.1039/C5CC02246K
	(c) Ye, Y.-Y.; Zhou, P.-X.; Luo, J.-Y.; Zhong, M.-J.; Liang, Y.-M. Chem. Commun. 2013, 49, 10190. doi: 10.1039/c3cc45583a
	(d) Zhou, P.-X.; Ye, Y.-Y.; Liang, Y.-M. Org. Lett. 2013, 15, 5080. doi: 10.1021/ol402457h
[13]	(a) Ren, X.; Zhu, L.; Yu, Y.; Wang, Z.-X.; Huang, X. Org. Lett. 2020, 22, 3251. doi: 10.1021/acs.orglett.0c01040
	(b) Zhu, L.; Ren, X.; Yu, Y.; Ou, P.; Wang, Z.-X.; Huang, X. Org. Lett. 2020, 22, 2087. doi: 10.1021/acs.orglett.0c00579
[14]	(a) Feng, J.; Li, B.; He, Y.; Gu, Z. Angew. Chem., nt. Ed. 2016, 55, 2186.
	(b) Chen, H.; Huang, L.; Fu, W.; Liu, X.; Jiang, H. Chem.-Eur. J. 2012, 18, 10497. doi: 10.1002/chem.v18.34
	(c) Zhou, F.; Ding, K.; Cai, Q. Chem.-Eur. J. 2011, 17, 12268. doi: 10.1002/chem.v17.44
	(d) Xu, K.; Shen, C.; Shan, S. Chin. J. Org. Chem. 2015, 35, 294. (in Chinese) doi: 10.6023/cjoc201409034
	(许恺, 沈冲, 单尚, 有机化学, 2015, 35, 294.) doi: 10.6023/cjoc201409034
[15]	(a) Bamford, W. R.; Stevens, T. S. J. Chem. Soc. 1952, 4735.
	(b) Arunprasath, D.; Sekar, G. Adv. Synth. Catal. 2017, 359, 698. doi: 10.1002/adsc.v359.4
[16]	(a) Harusawa, S.; Yoneda, R.; Omori, Y.; Kurihara, T. Tetrahedron Lett. 1987, 28, 4189.
	(b) Wang, Z.-H.; Ji, X.-M.; Hu, M.-L.; Tang, R.-Y. Tetrahedron Lett. 2015, 56, 5067.
[17]	Fulton, J. R.; Aggarwal, V. K.; de Vicente, J. Eur. J. Org. Chem. 2005, 1479.

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