Regioselective synthesis of 5H-thiazolo[3,2-a]pyrimidin-5-ones from Morita-Baylis-Hillman adduct acetates under solvent-free and base-free conditions

Synthesis

Volumn , Issue 10, 2009, Pages 1615-1622

  Zhong, Weihui ^a   Guo, Baoming ^a   Lin, Fuliang ^a   Liu, Yongliang ^a   Su, Weike ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

, unsaturated esters; Base free; Fused ring systems; Heterocycles; Solvent free; Thiazol 2 amines

Indexed keywords

BASE-FREE; FUSED-RING SYSTEMS; HETEROCYCLES; SOLVENT-FREE; THIAZOL-2-AMINES;

ADDITION REACTIONS; AMINATION; AMINES; ENERGY ABSORPTION; ESTERIFICATION; RATE CONSTANTS; SOLVENTS;

ESTERS;

5H THIAZOLO[3,2 A]PYRIMIDIN 5 ONE DERIVATIVE; ACETIC ACID; BENZYLIDENE 6,7 THIAZOLO[3,2 A]PYRIMIDIN 5 ONE DERIVATIVE; HETEROCYCLIC COMPOUND; NUCLEOPHILE; PYRIMIDINONE DERIVATIVE; REAGENT; THIAZOL 2 AMINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; MORITA BAYLIS HILLMAN REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; SYNTHESIS; TECHNIQUE; THERMO SIGMATROPIC PROTON SHIFT;

EID: 67650022825     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1088051     Document Type: Article

References (35)

1. (a) Sharma, V. P. Indian J. Heterocycl. Chem. 2004, 14, 35.
2. (b) Meinhardt, G.; Eppinger, E.; Schmidmaier, R. Anti-Cancer Drugs 2002, 13, 725.
3. (c) Jones, D. E.; Coates, J. A. V.; Rhodes, D. I.; Deadman, J. J.; Vandegrafe, N. A.; Winfield, L. J.; Thienthong, N.; Issa, W.; Choi, N.; Macfarlane, K. WO Patent 77188, 2008; Chem. Abstr. 2008, 149, 128851.
4. (d) Brough, P. A.; Cheetham, S. C.; Kerrigan, F.; Watts, J. P. WO Patent 71549, 2000; Chem. Abstr. 2000, 134, 29416.
5. (e) Yadav, R. K.; Mishra, A. R.; Wahab, A.; Mishra, R. M. Indian J. Heterocycl. Chem. 2007, 16, 305.
6. (f) Mohan, J.; Kumar, A. Indian J. Heterocycl. Chem. 2002, 11, 325.
7. Kennis, L. E. J.; Vandenberk, J.; Mertens, J. C. EP 110435, 1983; Chem. Abstr. 1984, 102, 6522.
8. (a) Novellino, E.; Cosimelli, B.; Ehlardo, M.; Greco, G.; Iadanza, M.; Lavecchia, A.; Rimoli, M. G.; Sala, A.; Settimo, A. D.; Primofiore, G.; Settimo, F. D.; Taliani, S.; Motta, C. L.; Klotz, K.; Tuscano, D.; Trincavelli, M. L.; Martini, C. J. Med. Chem. 2005, 48, 8253.
9. (b) Huang, X.; Liu, Z. J. Org. Chem. 2002, 67, 6731.
10. (c) Landreau, C.; Deniaud, D.; Meslin, J. C. J. Org. Chem. 2003, 68, 4912.
11. (d) Bibas, H.; Moloney, D. W. J.; Neumann, R.; Shtaiwi, M.; Bernhardt, P. V.; Wentrup, C. J. Org. Chem. 2002, 67, 2619.
12. (e) Erian, A. W.; Sherifa, S. M.; Mohamed, N. R. ARKIVOC 2001, (x), 85.
13. (f) Abdel-Hafez, S. H. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 2563.
14. (g) Toche, R. B.; Ghotekar, B. K.; Kazi, M. A.; Kendre, D. B.; Jachak, M. N. Tetrahedron 2007, 63, 8157.
15. (h) Jakše, R.; Svete, J.; Stanovnik, B.; Golobič, A. Tetrahedron 2004, 60, 4601.
16. (a) Basavaiah, D.; Rao, K. V.; Reddy, R. J. Chem. Soc. Rev. 2007, 36, 1581.
17. (b) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
18. (c) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
19. (d) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
20. (a) Lee, H. S.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2007, 48, 4119.
21. (b) Kim, S. J.; Lee, H. S.; Kim, J. N. Tetrahedron Lett. 2007, 48, 1069.
22. (c) Kabalka, G. W.; Venkataiah, B.; Dong, G. J. Org. Chem. 2004, 69, 5807.
23. (d) Gong, J. H.; Kim, H. R.; Ryu, H. R.; Kim, Y. N. Bull. Korean Chem. Soc. 2002, 23, 789.
24. (e) Im, Y. J.; Na, J. E.; Kim, J. N. Bull. Korean Chem. Soc. 2003, 24, 511.
25. (f) Basavaiah, D.; Reddy, R. J. Org. Biomol. Chem. 2008, 6, 1034.
26. (g) Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511.
27. (a) Zhong, W.; Zhao, Y.; Su, W. Tetrahedron 2008, 64, 5491.
28. (b) Zhong, W.; Lin, F.; Chen, R.; Su, W. Synthesis 2008, 2561.
29. (c) Zhong, W.; Zhao, Y.; Guo, B.; Su, W. Synth. Commun. 2008, 38, 3291.
30. (a) Clark, J. H. Green Chem. 2006, 8, 17.
31. (b) Sheldon, R. A. Green Chem. 2008, 10, 359.
32. (c) Maddessa, M. L.; Kilbinger, A. F. M. Chem. Commun. 2007, 31, 3231.
33. (d) Mosrin, M.; Boudet, N.; Knochel, P. Org. Biomol. Chem. 2008, 6, 3237.
34. For the preparation of thiazol-2-amines, see: (a) Furruiss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed., Vol. 2; Elsevier: Amsterdam, 1989, 1152.
35. (b) Allen, C. F. H.; VanAllan, J. Org. Synth. 1955, 3, 76.