Facile Access to α-Substituted β-Thio Enals from 1,2,3-Triazines and Thiols

Abstract

Herein, a chemoselective cascade addition reaction is reported, which starts from 1,2,3-triazines and thiols to access several different α-substituted β-thio enals and their derivatives in a green and efficient synthesis. In terms of applications, readily available substrates, diversity of products, and mild reaction system make this strategy highly attractive.

Key words

1,2,3-triazines - thiols - cascade reaction - thiolation - enals

Publication History

Received: 11 February 2022

Accepted after revision: 07 March 2022

Accepted Manuscript online:
07 March 2022

Article published online:
04 May 2022

• References

• 1a Funabiki K, Ohtake C, Muramatsu H, Matsui M, Shibata K. Synlett 1996; 444
• 1b Ramkumar K, Yarovenko VN, Nikitina AS, Zavarzin IV, Krayushkin MM, Kovalenko LV, Esqueda A, Odde S, Neamati N. Molecules 2010; 15: 3958
• 2a Wadhwa R, Sugihara T, Yoshida A, Nomura H, Reddel RR, Simpson R, Maruta H, Kaul SC. Cancer Res. 2000; 60: 6818
• 2b Faour L, Adam C, Gautier C, Goeb S, Allain M, Levillain E, Canevet D, Sallé M. Chem. Commun. 2019; 55: 5743
• 3a Lack NA, Axerio-Cilies P, Tavassoli P, Han FG, Chan KH, Feau C, LeBlanc E, Guns ET, Guy RK, Rennie PS, Cherkasov A. J. Med. Chem. 2012; 55: 565
• 3b Lilienkampf A, Karkola S, Alho-Richmond S, Koskimies P, Johansson N, Huhtinen K, Vihko K, Wahala K. J. Med. Chem. 2009; 52: 6660
• 4 Irgashev RA, Kazin NA, Rusinov GL. ACS Omega 2021; 6: 32277
• 5a Nafe J, Auras F, Karaghiosoff K, Bein T, Knochel P. Org. Lett. 2015; 17: 5356
• 5b Kondrashov EV, Romanov AR, Ushakov IA, Rulev AYu. J. Sulfur Chem. 2017; 38: 18
• 5c Chen H, Wang J, Feng X, Zhu M, Hoffmann S, Hsu A, Qian K, Huang D, Zhao F, Liu W, Zhang H, Cheng Z. Chem. Sci. 2019; 10: 7946
• 6a Marchese AD, Mirabi B, Larin EM, Lautens M.  Synthesis 2020; 52: 311
• 6b He L, Guo H, Li Y.-Z, Du G.-F, Dai B. Chem. Commun. 2014; 50: 3719
• 6c Zhu P, He X, Chen X, You Y, Yuan Y, Weng Z. Tetrahedron 2014; 70: 672
• 6d Chen Z, Jin W, Xia Y, Zhang Y, Xie M, Ma S, Liu C. Org. Lett. 2020; 22: 8261
• 7a Luo H, Tang Z, Wang T, Tian Y, Zhang Y, Li Y, Li S, Gong Y, Li B. Org. Chem. Front. 2020; 7: 3727
• 7b Luo H, Li Y, Du L, Xin X, Wang T, Han J, Tian Y, Li B. Org. Lett. 2021; 23: 7883
• 7c Li Y, Luo H, Tang Z, Li Y, Du L, Xin X, Li S, Li B. Org. Lett. 2021; 23: 6450
• 8a Zhang F.-G, Chen Z, Tang X, Ma J.-A. Chem. Rev. 2021; 121: 14555
• 8b Zhang J, Shukla V, Boger DL. J. Org. Chem. 2019; 84: 9397
• 9a Itoh T, Nagata K, Kaihoh T, Okada M, Kawabata C, Arai H, Ohnishi H, Yamaguchi K, Igeta H, Ohsawa A, Iitaka Y. Heterocycles 1992; 33: 631
• 9b Quiñones RE, Glinkerman CM, Zhu K, Boger DL. Org. Lett. 2017; 19: 3568
• 10a Sugita T, Koyama J, Tagahara K, Suzuta Y. Heterocycles 1985; 23: 2789
• 10b Itoh T, Ohsawa A, Okada M, Kaihoh T, Igeta H. Chem. Pharm. Bull. 1985; 33: 3050
• 10c Okatani T, Koyama J, Suzuta Y, Tagahara K. Heterocycles 1988; 27: 2213
• 10d Okatani T, Koyama J, Tagahara K. Heterocycles 1989; 29: 1809
• 10e Itoh T, Okada M, Nagata K, Yamaguchi K, Ohsawa A. Chem. Pharm. Bull. 1990; 38: 2108
• 10f Koyama J, Ogura T, Tagahara K. Heterocycles 1994; 38: 1595
• 11a Anderson ED, Boger DL. Org. Lett. 2011; 13: 2492
• 11b Anderson ED, Boger DL. J. Am. Chem. Soc. 2011; 133: 12285
• 11c Glinkerman CM, Boger DL. Org. Lett. 2015; 17: 4002
• 11d Zhang Y, Luo H, Lu Q, An Q, Li Y, Li S, Tang Z, Li B. Chin. Chem. Lett. 2021; 32: 393
• 12 Anderson ED, Duerfeldt AS, Zhu K, Glinkerman CM, Boger DL. Org. Lett. 2014; 16: 5084
• 13 Ohsawa A, Kaihoh T, Igeta H. J. Chem. Soc., Chem. Commun. 1985; 1370
• 14 Luo H, Li Y, Zhang Y, Lu Q, An Q, Xu M, Li S, Li J, Li B. J. Org. Chem. 2022; 87: 2590