Citation: Yuan Zhang, Han Luo, Qixing Lu, Qiaoyu An, You Li, Shanshan Li, Zongyuan Tang, Baosheng Li. Access to pyridines via cascade nucleophilic addition reaction of 1,2,3-triazines with activated ketones or acetonitriles[J]. Chinese Chemical Letters, ;2021, 32(1): 393-396. doi: 10.1016/j.cclet.2020.03.075 shu

Access to pyridines via cascade nucleophilic addition reaction of 1,2,3-triazines with activated ketones or acetonitriles

School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030, China

libs@cqu.edu.cn

Received Date: 26 February 2020
Revised Date: 25 March 2020
Accepted Date: 30 March 2020
Available Online: 14 May 2020

Figures(5)

We studied the cascade nucleophilic addition reactions of 1,2,3-triazines with activated acetonitriles or ketones, which were used to construct highly substituted pyridines that are not easily accessed by conventional methods. The strategy addressed some structural diversity issues currently facing medicinal chemistry, and the resulting pyridines could be used as convenient precursors for the synthesis of related pharmaceuticals. In particular, our method was applied to the syntheses of the marketed drug etoricoxib and several biologically important molecules in a few steps.
- 1,2,3-Triazines,
- Pyridines,
- Nucleophilic addition,
- Divergent synthesis,
- Pharmaceuticals synthesis
1. [1]
  (a) D. O'Hagan, Nat. Prod. Rep. 17 (2000) 435-446;
  (b) G.D. Henry, Tetrahedron 60 (2004) 6043-6061;
  (c) I. Nakamura, Y. Yamamoto, Chem. Rev. 104 (2004) 2127-2198;
  (d) M.H. Cao, N.J. Green, S.Z. Xu, Org. Biomol. Chem. 15 (2017) 3105-3129;
  (e) L. Li, Z. Chen, X. Zhang, Y. Jia, Chem. Rev. 118 (2018) 3752-3832.
2. [2]
  (a) W. Du, Tetrahedron 59 (2003) 8649-8687;
  (b) K.V. Sashidhara, R.K. Modukuri, D. Choudhary, et al., Eur. J. Med. Chem. 70 (2013) 802-810;
  (c) E. Vitaku, D.T. Smith, J.T. Njardarson, J. Med. Chem. 57 (2014) 10257-10274;
  (d) D. Verga, C.H. NâGuyen, M. Dakir, et al., J. Med. Chem. 61 (2018) 10502-10518.
3. [3]
  C.E. Müller, P.R. Schreiner, Angew. Chem. Int. Ed. 50 (2011) 6012-6042.
4. [4]
  (a) C. Kaes, A. Katz, M.W. Hosseini, Chem. Rev. 100 (2000) 3553-3590;
  (b) G. Chelucci, R. Thummel, Chem. Rev. 102 (2002) 3129-3170.
5. [5]
  J.A. Bull, J.J. Mousseau, G. Pelletier, A.B. Charette, Chem. Rev. 112 (2012) 2642-2713.
6. [6]
  (a) Z. Shi, T.P. Loh, Angew. Chem. Int. Ed. 52 (2013) 8584-8587;
  (b) J. Chen, Q. Song, C. Wang, Z. Xi, J. Am. Chem. Soc. 124 (2002) 6238-6239;
  (c) J.A. Varela, C. Saá, Chem. Rev. 103 (2003) 3787-3802;
  (d) G. Domínguez, J. Pérez-Castells, Chem. Soc. Rev. 40 (2011) 3430-3444;
  (e) N.S.Y. Loy, A. Singh, X. Xu, C.M. Park, Angew. Chem. Int. Ed. 52 (2013) 2212-2216;
  (f) A. Prechter, G. Henrion, P.F. dit Bel, F. Gagosz, Angew. Chem. Int. Ed. 53 (2014) 4959-4959.
7. [7]
  (a) A. Ohsawa, T. Kaihoh, H. Igeta, Chem. Commun. (1985) 1370-1371;
  (b) T. Kaihoh, T. Itoh, A. Ohsawa, et al., Chem. Phar. Bull. 35 (1987) 3952-3954;
  (c) T. Itoh, K. Nagata, T. Kaihoh, et al., Heterocycles 33 (1992) 631-639;
  (d) E.D. Anderson, A.S. Duerfeldt, K. Zhu, C.M. Glinkerman, D.L. Boger, Org. Lett. 16 (2014) 5084-5087;
  (e) C.M. Glinkerman, D.L. Boger, Org. Lett. 17 (2015) 4002-4005;
  (f) E.D. Anderson, D.L. Boger, Org. Lett. 13 (2011) 2492-2494;
  (g) E.D. Anderson, D.L. Boger, J. Am. Chem. Soc. 133 (2011) 12285-12292.
8. [8]
  (a) T. Sugita, J. Koyama, K. Tagahara, Y. Suzuta, Heterocycles 23 (1985) 2789-2791;
  (b) T. Sugita, J. Koyama, K. Tagahara, Y. Suzuta, Heterocycles 24 (1986) 29-30;
  (c) T. Okatani, J. Koyama, K. Tagahara, Y. Suzuta, Heterocycles 26 (1987) 595-597;
  (d) T. Okatani, J. Koyama, Y. Suzuta, K. Tagahara, Heterocycles 27 (1988) 2213-2217;
  (e) T. Okatani, J. Koyama, K. Tagahara, Heterocycles 29 (1989) 1809-1814;
  (f) J. Koyama, T. Ogura, K. Tagahara, Heterocycles 38 (1994) 1595-1600;
  (g) A. Díaz-Oritz, A. de la Hoz, P. Prieto, et al., Synlett 2 (2001) 236-237.
9. [9]
  (a) T. Itoh, A. Ohsawa, M. Okada, T. Kaihoh, H. Igeta, Chem. Pharm. Bull. 33 (1985) 3050-3052;
  (b) T. Itoh, M. Okada, K. Nagata, K. Yamaguchi, A. Ohsawa, Chem. Pharm. Bull. 38 (1990) 2108-2111.
10. [10]
  (a) A. Ohsawa, H. Arai, H. Ohnishi, H. Igeta, Chem. Commun. (1980) 1182-1183;
  (b) A. Ohsawa, H. Arai, H. Ohnishi, H. Igeta, Chem. Commun. (1981) 1174-1174;
  (c) A. Ohsawa, H. Arai, H. Ohnishi, et al., J. Org. Chem. 50 (1985) 5520-5523;
  (d) A. Ohsawa, T. Kaihoh, T. Itoh, et al., Chem. Pharm. Bull. 36 (1988) 3838-3848.
11. [11]
  (a) H. Neunhoeffer, M. Clausen, H.D. Vöetter, et al., Liebigs Ann. Chem. (1985) 1732-1751;
  (b) H. Neunhoeffer, R. Bopp, W. Diehl, Liebigs Ann. Chem. (1993) 367-373;
  (c) M. M. Mättner, H. Neunhoeffer, Synthesis (2003) 413-425.
12. [12]
  (a) A.S. Duerfeldt, D.L. Boger, J. Am. Chem. Soc. 136 (2014) 2119-2125;
  (b) C.M. Glinkerman, D.L. Boger, J. Am. Chem. Soc. 138 (2016) 12408-12413;
  (c) J. Zhang, V. Shukla, D.L. Boger, J. Org. Chem. 84 (2019) 9397-9445.
13. [13]
  D.P. Becker, D.L. Flynn, A.E. Moormann, et al., J. Med. Chem. 49 (2006) 1125-1139.
14. [14]
  (a) D.Dubé, R.Fortin, R.Friesen, J.Y.Gauthier, Z. Wang, WO9803484A1, (1998);
  (b) R.W. Friesen, C. Brideau, C.C. Chan, et al., Bioorg. Med. Chem. Lett. 8 (1998) 2777-2782;
  (c) I.W. Davies, J.F. Marcoux, E.G. Corley, et al., J. Org. Chem. 65 (2000) 8415-8420;
  (d) E. Zhang, J. Tang, S. Li, et al., Chem. Eur. J. 22 (2016) 5692-5697.
15. [15]
  (a) S.P. Mercer, A.J. Roecker, S. Garson, et al., Bioorg. Med. Chem. Lett. 23 (2013) 6620-6624;
  (b) A.J. Roecker, S.P. Mercer, J.D. Schreier, et al., ChemMedChem 9 (2014) 311-322.
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