A facile and practical one-pot synthesis of β-oxo thioamides from β-oxo amides and isothiocyanates

Synthesis

Volumn , Issue 11, 2009, Pages 1797-1800

  Huang, Peng ^a   Xiang, Dexuan ^b   Zhou, Yang ^a   Liang, Yongjiu ^a   Na, Tianhai ^a   Dong, Dewen ^a,b  

^a CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^b NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

3 oxo amides; Ethanol; Isothiocyanates; Potassium carbonate; Thioamides

Indexed keywords

3-OXO AMIDES; HIGH YIELD; ISOTHIOCYANATES; ONE-POT SYNTHESIS; POTASSIUM CARBONATE; POTASSIUM CARBONATES; THIOAMIDES;

CARBONATION; ETHANOL; POTASH; POTASSIUM;

AMIDES;

ISOTHIOCYANIC ACID DERIVATIVE; POTASSIUM CARBONATE; THIOAMIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS;

EID: 67650087548     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1088078     Document Type: Article

References (47)

1. (a) Bauer, W.; Kühlein, K. In Houben-Weyl, Vol. E5; Falbe, J., Ed.; Thieme: Stuttgart, 1985, 1218-1279.
2. (b) Schaumann, E. In Comprehensive Organic Synthesis, Vol. 6; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, 419-434.
3. For reviews on the synthesis and applications of thioamides, see: (a) Hurd, R. N.; Delamater, G. Chem. Rev. 1961, 61, 45.
4. (b) Walter, W.; Bode, K.-D. Angew. Chem., Int. Ed. Engl. 1966, 5, 447.
5. (c) Takahata, H.; Yamazaki, T. Heterocycles 1988, 27, 1953.
6. (d) Jagodzinski, T. S. Chem. Rev. 2003, 103, 197.
7. For selected examples, see: (a) Kolakowski, R. V.; Shangguan, N.; Williams, L. J. Tetrahedron Lett. 2006, 47, 1163.
8. (b) Varma, R. S.; Kumar, D. Org. Lett. 1999, 1, 697.
9. (c) Zbruyev, O. I.; Stiasni, N.; Kappe, C. O. J. Comb. Chem. 2003, 5, 145.
10. (d) Brain, C. T.; Hallett, A.; Ko, S. Y. J. Org. Chem. 1997, 62, 3808.
11. (e) Charette, A. B.; Grenon, M. J. Org. Chem. 2003, 68, 5792.
12. (f) Pfund, E.; Masson, S.; Vazeux, M.; Lequeux, T. J. Org. Chem. 2004, 69, 4670.
13. (g) Kaleta, Z.; Makowski, B. T.; Soos, T.; Dembinski, R. Org. Lett. 2006, 8, 1625.
14. (h) Kaboudin, B.; Elhamifar, D. Synthesis 2006, 224.
15. Brillon, D. Sulfur Rep. 1992, 12, 297.
16. (a) Scheeren, J. W.; Ooms, P. H. J.; Nivard, R. J. F. Synthesis 1973, 149.
17. (b) Dash, B.; Dora, E. K.; Panda, C. S. Heterocycles 1982, 19, 2093.
18. (c) Cava, M. P.; Levinson, M. I. Tetrahedron 1985, 41, 5061.
19. (d) Jones, B. A.; Bradshaw, J. S. Chem. Rev. 1984, 84, 17.
20. (a) Hartke, K.; Gerber, H.-D. J. Prakt. Chem. 1996, 338, 763.
21. (b) Raucher, S.; Klein, P. J. Org. Chem. 1981, 46, 3558.
22. (c) Brillon, D. Synth. Commun. 1990, 20, 3085.
23. (d) Goel, O. P.; Krolls, U. Synthesis 1987, 162.
24. (e) Curphey, T. J. J. Org. Chem. 2002, 67, 6461.
25. (a) Ogata, M.; Matsumoto, H. Heterocycles 1978, 11, 139.
26. (b) Hirabayashi, T.; Inoue, K.; Yokota, K. J. Organomet. Chem. 1975, 92, 139.
27. (c) Steliou, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104.
28. (d) Wojtkowski, P. W.; Dolfini, J. E.; Kocy, O.; Cimarusti, C. M. J. Am. Chem. Soc. 1975, 97, 5628.
29. (a) Ilankumaran, P.; Ramesha, A. R.; Chandrasekaran, S. Tetrahedron Lett. 1995, 36, 8311.
30. (b) Smith, D. C.; Lee, S. W.; Fuchs, P. L. J. Org. Chem. 1994, 59, 348.
31. (c) Bodine, J. J.; Kaloustian, M. Synth. Commun. 1982, 12, 787.
32. Ley, S. V.; Leach, A. G.; Storer, R. I. J. Chem. Soc., Perkin Trans. 1 2001, 358.
33. (a) Jagodziński, T. Synthesis 1988, 717.
34. (b) Jagodziński, T. Org. Prep. Proced. Int. 1990, 22, 755.
35. (c) Jagodziński, T.; Jagodzińska, E.; Jabłoń ski, Z. Tetrahedron 1986, 42, 3683.
36. Liang, F.; Li, Y.; Li, D.; Cheng, X.; Liu, Q. Tetrahedron Lett. 2007, 48, 7938.
37. For reviews on the synthesis and applications of α-oxo ketene S,S-acetals, see: (a) Dieter, R. K. Tetrahedron 1986, 42, 3029.
38. (b) Junjappa, H.; Ila, H.; Asokan, C. V. Tetrahedron 1990, 46, 5423.
39. (c) Kolb, M. Synthesis 1990, 171.
40. (a) Dong, D.; Ouyang, Y.; Yu, H.; Liu, Q.; Liu, J.; Wang, M.; Zhu, J. J. Org. Chem. 2005, 70, 4535.
41. (b) Liu, Q.; Che, G.; Yu, H.; Liu, Y.; Zhang, J.; Zhang, Q.; Dong, D. J. Org. Chem. 2003, 68, 9148.
42. (c) Yu, H.; Liu, Q.; Yin, Y.; Fang, Q.; Zhang, J.; Dong, D. Synlett 2004, 999.
43. (d) Sun, R.; Liu, Q.; Yu, H.; Zhao, Y.; Liu, J.; Ouyang, Y.; Dong, D. Chin. J. Chem. 2005, 23, 1060.
44. (a) Barnikow, G. J. Prakt. Chem. 1966, 34, 251.
45. (b) Zankowska-Jasińska, W.; Gałuszka, B. J. Fluorine Chem. 1983, 22, 165.
46. (a) Foye, W. O. J. Chem. Ed. 1969, 46, 841.
47. (b) Larsson, F. C. V.; Lawesson, S. O. Tetrahedron 1972, 28, 5341.