A facile and efficient synthesis of fully substituted pyridin-2(1H)-ones from α-oxoketene-S,S-acetals

Tetrahedron

Volumn 67, Issue 43, 2011, Pages 8343-8347

  Yang, Xiuyun ^a   Cheng, Yanyan ^a   Zhao, Fei ^c   Li, Yunhui ^a   Ding, Yuanli ^a   Liang, Yongjiu ^b   Gan, Fengjiao ^a   Dong, Dewen ^b  

^a CHANGCHUN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^c NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 [BIS(ETHYLTHIO)METHYLENE] 3 OXO N PHENYLBUTANAMIDE; 2 AMINO 1 (2 CHLOROPHENYL) 5 [2,2 DICYANO 1 (ETHYLTHIO)VINYL] 4 METHYL 6 OXO 1,6 DIHYDROPYRIDINE 3 CARBONITRILE; 2 AMINO 1 (4 CHLOROPHENYL) 5 [2,2 DICYANO 1 (ETHYL THIO)VINYL] 4 METHYL 6 OXO 1,6 DIHYDROPYRIDINE 3 CARBONITRILE; 2 AMINO 5 [1 (BENZYLTHIO) 2,2 DICYANOVINYL] 1 (2 METHOXYPHENYL) 4 METHYL 6 OXO 1,6 DIHYDROPYRIDINE 3 CARBONITRILE; 2 AMINO 5 [1 (BENZYLTHIO) 2,2 DICYANOVINYL] 4 METHYL 6 OXO 1 PHENYL 1,6 DIHYDROPYRIDINE 3 CARBONITRILE; 2 AMINO 5 [2,2 DICYANO 1 (ETHYLTHIO)VINYL] 1 (2 METHOXYPHENYL) 4 METHYL 6 OXO 1,6 DIHYDROPYRIDINE 3 CARBONITRILE; 2 AMINO 5 [2,2 DICYANO 1 (ETHYLTHIO)VINYL] 1 (2,4 DI METHYLPHENYL) 4 METHYL 6 OXO 1,6 DIHYDROPYRIDINE 3 CARBONITRILE; 2 AMINO 5 [2,2 DICYANO 1 (ETHYLTHIO)VINYL] 1 (4 METHOXYPHENYL) 4 METHYL 6 OXO 1,6 DIHYDROPYRIDINE 3 CARBONITRILE; 2 AMINO 5 [2,2 DICYANO 1 (ETHYLTHIO)VINYL] 4 METHYL 6 OXO 1 2 TOLYL 1,6 DIHYDROPYRIDINE 3 CARBONITRILE; 2 AMINO 5 [2,2 DICYANO 1 (ETHYLTHIO)VINYL] 4 METHYL 6 OXO 1 4 TOLYL 1,6 DIHYDROPYRIDINE 3 CARBONITRILE; 2 AMINO 5 [2,2 DICYANO 1 (ETHYLTHIO)VINYL] 4 METHYL 6 OXO 1 PHENYL 1,6 DIHYDROPYRIDINE 3 CARBONITRILE; 2 AMINO 5 [2,2 DICYANO 1 (METHYLTHIO)VINYL] 1 (2 METHOXYPHENYL) 4 METHYL 6 OXO 1,6 DIHYDROPYRIDINE 3 CARBONITRILE; 2 AMINO 5 [2,2 DICYANO 1 (METHYLTHIO)VINYL] 4 METHYL 6 OXO 1 PHENYL 1,6 DIHYDROPYRIDINE 3 CARBONITRILE; ACETAL DERIVATIVE; ALPHA OXOKETENE ACETAL DERIVATIVE; MALONONITRILE; METHANOL; PYRIDIN 2(1H) ONE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ONE POT SYNTHESIS; PRIORITY JOURNAL;

EID: 80053051601     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.08.066     Document Type: Article

References (65)

1. A.D. Elbein, and R.J. Molyneux S.W. Pelletier, Alkaloids: Chemical and Biological Perspectives Vol. 5 1981 Wiley New York, NY 1 54
2. M. Nagarajan, X. Xiao, S. Anotony, G. Kohlhagen, Y. Pommier, and M. Cushman J. Med. Chem. 46 2003 5712
3. Q. Li, L.A. Mitscher, and L.L. Shen Med. Res. Rev. 20 2000 231
4. G. Jones A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II Vol. 5 1996 Pergamon Oxford 167 243
5. G. Jones Pyridines and their benzo derivatives: synthesis A. Boulton, A. McKillop, Comprehensive Heterocyclic Chemistry 1984 Pergamon Oxford 395 510 Chapter 2.08
6. L.M. José, M. Karina, J. Cecilia, and C.P. Rafael ChemMedChem 2 2007 1141
7. L. Jayasinghe, H.K. Abbas, M.R. Jacob, W. Herath, and N.P.D. Nanayakkara J. Nat. Prod. 69 2006 439
8. F. Liang, X. Cheng, J. Liu, and Q. Liu Chem. Commun. 2009 3636
9. H. Schirok, C. Alonso-Alija, J. Benet-Buchholz, A.H. Göller, R. Grosser, M. Michels, and H. Paulsen J. Org. Chem. 70 2005 9463
10. M. Torres, S. Gil, and M. Parra Curr. Org. Chem. 9 2005 1757
11. P.R. Angibaud, M.G. Venet, W. Filliers, R. Broeckx, Y.A. Ligny, P. Muller, V.S. Poncelet, and D.W. End Eur. J. Org. Chem. 2004 479
12. R.E. Dolle, and K.C. Nicolaou J. Am. Chem. Soc. 107 1985 1691
13. R.J. Cox, and D. Ohagan J. Chem. Soc., Perkin Trans. 1 1991 2537
14. H. Decker Chem. Ber. 25 1892 443
15. D.L. Comins, and J.K. Saha J. Org. Chem. 61 1996 9623
16. W. Du Tetrahedron 59 2003 8649
17. H.-J. Cristau, P.P. Cellier, J.-F. Spindler, and M. Taillefer Chem. - Eur. J. 10 2004 5607
18. H. Baron, F.G.P. Remfry, and J.F. Thorpe J. Chem. Soc. 85 1904 1726
19. V. Aggarwal, G. Singh, H. Ila, and H. Junjappa Synthesis 1982 214
20. K.R. Gibson, L. Hitzel, R.J. Mortishire-Smith, U. Gerhard, R.A. Jelley, A.J. Reeve, M. Rowley, A. Nadin, and A.P. Owens J. Org. Chem. 67 2002 9354
21. D. Xiang, K. Wang, Y. Liang, G. Zhou, and D. Dong Org. Lett. 10 2008 345
22. D. Xiang, Y. Yang, R. Zhang, Y. Liang, W. Pan, J. Huang, and D. Dong J. Org. Chem. 72 2007 8593
23. R. Zhang, D. Zhang, Y. Guo, G. Zhou, Z. Jiang, and D. Dong J. Org. Chem. 73 2008 9504
24. A. Robin, K. Julienne, J.C. Meslin, and D. Deniaud Tetrahedron Lett. 45 2004 9557
25. F. Sainte, B. Serckx-Poncin, A.M. Hesbain-Frisque, and L. Ghosez J. Am. Chem. Soc. 104 1982 1428
26. K.H. Chung, K.Y. Cho, Y. Asami, N. Takahashi, and S. Yoshida Heterocycles 32 1991 99
27. J.A. Varela, and C. Saa Chem. Rev. 103 2003 3787
28. Y. Yamamoto, H. Takagishi, and K. Itoh Org. Lett. 3 2001 2117
29. A. Padwa, T.M. Heidelbaugh, and J.T. Kuethe J. Org. Chem. 65 2000 2368
30. A. Padwa, S.M. Sheehan, and C.S. Straub J. Org. Chem. 64 1999 8648
31. E.R. Anabha, and C.V. Asokan Synthesis 2006 151
32. S. Chakrabarti, K. Panda, N.C. Misara, H. Ila, and H. Junjappa Synlett 2005 1437
33. P.K. Mahata, U.K. Syam, V. Kumar Sriram, H. Ila, and H. Junjappa Tetrahedron 59 2003 2631
34. H. Schirok, C. Alonso-Alija, and M. Michels Synthesis 2005 3085
35. L. Chen, Y. Zhao, Q. Liu, C. Cheng, and C. Piao J. Org. Chem. 72 2007 9259
36. For reviews on the synthesis and application of α-oxoketene-S,S- acetals, see: R.K. Dieter Tetrahedron 42 1986 3029
37. Y. Tominaga J. Heterocycl. Chem. 46 1989 143
38. H. Junjappa, H. Ila, and C.V. Asokan Tetrahedron 46 1990 5423
39. M. Kolb Synthesis 1990 171
40. H. Junjappa, and H. Ila Phosphorous, Sulfur Silicon 95 1994 35
41. H. Junjappa, H. Ila, and P.K. Mohanta G.H. Gribble, L.T. Gilchrist, Progress in Heterocyclic Chemistry Vol. 13 2001 Pergamon Oxford 1 24 Chapter 1
42. Y. Yang, D. Xiang, X. Zhao, Y. Liang, J. Huang, and D. Dong Tetrahedron 64 2008 4959
43. S. Sun, Y. Liu, Q. Liu, Y. Zhao, and D. Dong Synlett 2004 1731
44. Y. Liu, D. Dong, Q. Liu, Y. Qi, and Z. Wang Org. Biomol. Chem. 2 2004 28
45. Y. Ouyang, J. Huang, W. Pan, Y. Liang, Y. Yang, and D. Dong Eur. J. Org. Chem. 2009 2003
46. X. Bi, Q. Liu, S. Sun, J. Liu, W. Pan, L. Zhao, and D. Dong Synlett 2005 49
47. J. Huang, Y. Lu, B. Qiu, Y. Liang, N. Li, and D. Dong Synthesis 2007 2791
48. X. Bi, D. Dong, Q. Liu, W. Pan, L. Zhao, and B. Li J. Am. Chem. Soc. 127 2005 4578
49. D. Dong, X. Bi, Q. Liu, and F. Cong Chem. Commun. 2005 3580
50. X. Bi, D. Dong, Y. Li, Q. Liu, and Q. Zhang J. Org. Chem. 70 2005 10886
51. W. Pan, D. Dong, Y. Ouyang, R. Wu, Y. Yang, and Q. Liu Synthesis 2007 2115
52. Y. Ouyang, D. Dong, H. Yu, Y. Liang, and Q. Liu Adv. Synth. Catal. 348 2006 206
53. C.F. Bernasconi Tetrahedron 45 1989 4017
54. C.F. Bernasconi, D.F. Schuck, R.J. Ketner, I. Eventova, and Z. Rappoport J. Am. Chem. Soc. 117 1995 2719
55. J.E. Baldwin, R.M. Adlington, C. Aurelia, I. Nageswara Rao, R. Marquez, and G.J. Pritchard Org. Lett. 4 2002 2125
56. C.F. Bernasconi, S.D. Brown, M. Ali, Z. Rappoport, H. Yamataka, and H. Salim J. Org. Chem. 71 2006 4795
57. D. Dong, H. Yu, Y. Ouyang, Q. Liu, X. Bi, and Y. Lu Synlett 2006 283
58. D. Dong, Y. Ouyang, H. Yu, Q. Liu, J. Liu, M. Wang, and J. Zhu J. Org. Chem. 70 2005 4535
59. H. Yu, Q. Liu, Y. Yin, Q. Fang, J. Zhang, and D. Dong Synlett 2004 999
60. Q. Liu, G. Che, H. Yu, Y. Liu, J. Zhang, Q. Zhang, and D. Dong J. Org. Chem. 68 2003 9148
61. G. Jones R. Adams, The Knoevenagel Condensation Organic Reactions Vol. 15 1967 John Wiley New York, N Y 204 599
62. For the reactions of malononitrile, see: F. Freeman Chem. Rev. 69 1969 591
63. F. Freeman Chem. Rev. 80 1980 329
64. F. Liang, X. Cheng, J. Liu, and Q. Liu Chem. Commun. 2009 3636
65. P. Langer, and G. Bose Angew. Chem., Int. Ed. 42 2003 4033