Efficient synthesis of substituted tetrahydrothiopyrano[2,3-b]thiopyran-4, 5-diones by a double annulation strategy from dialkenoylketene dithioacetals

Synthesis

Volumn , Issue 14, 2007, Pages 2115-2120

  Pan, Wei ^a   Dong, Dewen ^a,b   Ouyang, Yan ^a   Wu, Rigenhada ^a   Yang, Yang ^a   Liu, Qun ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

^b CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

Author keywords

Amines; Annulations; Dialkenoylketene dithioacetals; Sodium hydride; Sodium sulfide

Indexed keywords

ANNULATION STRATEGY; DIALKENOYLKETENE DITHIOACETALS; SODIUM HYDRIDES; SODIUM SULFIDES;

REACTION KINETICS; SODIUM COMPOUNDS; SUBSTITUTION REACTIONS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

AMINES;

2,3,6,7 TETRAHYDROTHIOPYRANO[2,3 B]THIOPYRAN 4,5 DIONE DERIVATIVE; AMINE; KETENE DERIVATIVE; N,N DIMETHYLFORMAMIDE; PYRONE DERIVATIVE; SILICA GEL; SODIUM SULFIDE; THIOACETALDEHYDE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GEL CHROMATOGRAPHY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 34547161900     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983749     Document Type: Article

References (40)

1. (a) Ingall, A. H. In Comprehensive Heterocyclic Chemistry II, Vol. 5; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. W., Eds.; Pergamon: Oxford, 1996, 501.
2. (b) Vedejs, E.; Krafft, G. A. Tetrahedron 1982, 38, 2857.
3. (c) Hollick, J. J.; Golding, B. T.; Hardcastle, I. R.; Martin, N.; Richardson, C.; Rigoreau, L. J. M.; Smith, G. C. M.; Griffin, R. J. Bioorg. Med. Chem. Lett. 2003, 13, 3083.
4. Casy, G.; Taylor, R. J. K. Tetrahedron 1989, 45, 455.
5. Fujisawa, T.; Mobele, B. I.; Shimizu, M. Tetrahedron Lett. 1992, 33, 5567.
6. (a) McDonald, B. P.; Steele, R. W.; Sutherland, J. K.; Leslie, B. W.; Brewster, A. J. Chem. Soc., Perkin Trans. 1 1988, 675.
7. (b) Lawson, K. R.; McDonald, B. P.; Mills, O. S.; Steele, R. W.; Sutherland, J. K.; Wear, T. J.; Brewster, A.; Marsham, P. R. J. Chem. Soc., Perkin Trans. 1 1988, 663.
8. (a) McAllister, G. D.; Taylor, R. J. K. Tetrahedron Lett. 2001, 42, 1197.
9. (b) Taylor, R. J. K. Chem. Commun. 1999, 217.
10. (c) Matsuyama, H.; Miyazawa, Y.; Takei, Y.; Kobayashi, M. J. Org. Chem. 1987, 52, 1703.
11. (d) Matsuyama, H.; Fujii, S.; Kamigata, N. Heterocycles 1991, 32, 1875.
12. Chen, C. H.; Doney, J. J.; Reynolds, G. A. J. Org. Chem. 1981, 46, 4604.
13. Augustin, M.; Jahreis, G.; Rudorf, W. D. Synthesis 1977, 472.
14. (a) Ward, D. E.; Gai, Y. Z. Tetrahedron Lett. 1992, 33, 1851.
15. (b) Ward, D. E.; Nixey, T. E. Tetrahedron Lett. 1993, 34, 947.
16. (c) Ward, D. E.; Zoghaib, W. M.; Rhee, C. K.; Gai, Y. Z. Tetrahedron Lett. 1990, 31, 845.
17. (a) Barluenga, J.; Aznar, F.; Valdes, C. Synlett 1991, 487.
18. (b) Vedejs, E.; Eberlein, T. H.; Mazur, D. J.; McClure, C. K.; Perry, D. A.; Ruggeri, R.; Schwartz, E.; Stults, J. S.; Varie, D. L.; Wilde, R. G.; Wittenberger, S. J. Org. Chem. 1986, 51, 1556.
19. Samuel, R.; Nair, S. K.; Asokan, C. V. Synlett 2000, 1804.
20. For reviews on the synthesis and application of α-oxo ketene dithioacetals, see: (a) Dieter, R. K. Tetrahedron 1986, 42, 3029.
21. (b) Tominaga, Y. J. Heterocycl. Chem. 1989, 26, 1167.
22. (c) Junjappa, H.; Ila, H.; Asokan, C. V. Tetrahedron 1990, 46, 5423.
23. (d) Kolb, M. Synthesis 1990, 171.
24. (e) Junjappa, H.; Ila, H. Phosphorous, Sulfur Silicon Relat. Elem. 1994, 95, 35.
25. (f) Junjappa, H.; Ila, H.; Mohanta, P. K. In Progress in Heterocyclic Chemistry, Vol. 13; Gribble, G. H.; Gilchrist, L. T., Eds.; Pergamon: Oxford, 2001, Chap. 1, 1-24.
26. For selected examples of our recent work on α-oxo ketene dithioacetals, see: (a) Ouyang, Y.; Dong, D.; Yu, H.; Liang, Y.; Liu, Q. Adv. Synth. Catal. 2006, 348, 206.
27. (b) Dong, D.; Ouyang, Y.; Yu, H.; Liu, Q.; Liu, J.; Wang, M.; Zhu, J. J. Org. Chem. 2005, 70, 4535.
28. (c) Liu, Q.; Che, G.; Yu, H.; Liu, Y.; Zhang, J.; Zhang, Q.; Dong, D. J. Org. Chem. 2003, 68, 9148.
29. (d) Zhao, Y.; Liu, Q.; Zhang, J.; Liu, Z. J. Org. Chem. 2005, 70, 6913.
30. (e) Li, Y.; Liang, F.; Bi, X.; Liu, Q. J. Org. Chem. 2006, 71, 8006.
31. (f) Liang, Y.; Liu, Q. Adv. Synth. Catal. 2006, 348, 1986.
32. Formal [5+1] annulations of alkenoylketene dithioacetals see: (a) Bi, X.; Dong, D.; Liu, Q.; Pan, W.; Zhao, L.; Li, B. J. Am. Chem. Soc. 2005, 127, 4578.
33. (b) Dong, D.; Bi, X.; Liu, Q.; Cong, F. Chem. Commun. 2005, 3580.
34. (c) Bi, X.; Dong, D.; Li, Y.; Liu, Q.; Zhang, Q. J. Org. Chem. 2005, 70, 10886.
35. (d) Zhao, L.; Liang, F.; Bi, X.; Sun, S.; Liu, Q. J. Org. Chem. 2006, 71, 1094.
36. Ouyang, Y.; Dong, D.; Pan, W.; Zhang, J.; Liu, Q. Tetrahedron 2006, 62, 10111.
37. Ja Augustin, M.; Groth, Ch. J. Prakt. Chem. 1979, 321, 215.
38. Nair, S. K.; Samuel, R.; Asokan, C. V. Synthesis 2001, 573.
39. Bernasconi, C. F. Tetrahedron 1989, 45, 4017.
40. Ogurtsov, V. A.; Rakitin, O. A.; Rees, C. W.; Smolentsev, A. A.; Belyyakov, P. A.; Golovanov, D. G.; Lyssenko, K. A. Org. Lett. 2005, 7, 791.