Regioselectivity of the reactions of 4,5-diphenylimidazole-2-thione with 1-chloro-2,3-epoxy-propane and 1-bromo-propene, efficient precursors for imidazo[2,1-b]thiazine and thiazole. Effect of microwave and solid support

Journal of Heterocyclic Chemistry

Volumn 45, Issue 5, 2008, Pages 1321-1327

  Aouad, Mohamed R ^c   Rezki, Nadjet ^c   El Ahsry, El Sayed H ^a,b  

^a Alexandria University Faculty Of Science   (Egypt)

^b UNIVERSITY OF KARACHI   (Pakistan)

^c UNIVERSITÉ DES SCIENCES ET DE LA TECHNOLOGIE D ORAN MOHAMED BOUDIAF   (Algeria)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3 CHLORO 2 HYDROXYPROP 1 YL) 2 THIOBENZYL 4,5 DIPHENYLIMIDAZOLE; 1 (3 CHLORO 2 HYDROXYPROP 1 YL) 2 THIOMETHYL 4,5 DIPHENYLIMIDAZOLE; 1 ALLYL 2 THIOALLYL 4,5 DIPHENYLIMIDAZOLE; 1 ALLYL 2 THIOBENZYL 4,5 DIPHENYLIMIDAZOLE; 1 ALLYL 2 THIOMETHYL 4,5 DIPHENYLIMIDAZOLE; 1 BROMO PROPENE; 1 CHLORO 2,3 EPOXY PROPANE; 2,3 EPOXYPROPYLTHIOIMIDAZOLE; 4,5 DIPHENYL 2 THIOALLYLIMIDAZOLE; 4,5 DIPHENYL 2 THIOBENZYLIMIDAZOLE; 4,5 DIPHENYL 2 THIOMETHYLIMIDAZOLE; 4,5 DIPHENYL 2 THIOMETHYLOXIRANEIMIDAZOLE; 4,5 DIPHENYLIMIDAZOLE 2 THIONE; 5,6 DIPHENYL 2H,3H 3 METHYLTETRAHYDROIMIDAZO[2,1,B][1,3]THIAZOLE; 6,7 DIPHENYL 2H,3H,4H 3 HYDROXYTETRAHYDROIMIDAZO[2,1,B][1,3]THIAZINE; ANTIINFECTIVE AGENT; EPICHLOROHYDRIN; ETHYLENE OXIDE; IMIDAZO[2,1 B]THIAZINE; IMIDAZOLE DERIVATIVE; POTASSIUM CARBONATE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ALLYLATION; ARTICLE; CATALYST; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; MICROWAVE IRRADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RING CLOSING METATHESIS;

EID: 51849129211     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570450511     Document Type: Article

References (49)

1. (a) Greenlee, W. J.; Siegl, P. K. S. Annu. Rep. Med. Chem. 1992, 27, 59;
2. (b) Shilcrat, S. C.; Mokhallalati, M. K.; Fortinak, J. M. D.; Pridgen, L. N. J. Org. Chem. 1997, 62, 8449;
3. (c) Rizzi, J. P.; Nagel, A. A.; Rosen, T. ; Mc Lean, S.; Seeger, T. J. Med. Chem. 1990, 33, 2721;
4. (d) Shapiro, G.; Gomez-Lor, B. J. J. Org. Chem. 1944, 59, 5542.
5. (a) Weinberg, E. D. Antifungal Agents. Burger's Medicinal Chemistry and Drug Discovery, 5th ed.; Wiley Interscience: New York 1996; Vol. 2, pp 637-652;
6. (b) Fungal Infections: Dermatomycoses. Drug R&D Backgrounder 2001, 1, 57-66.
7. (a) Taurog, A. Endocrinology 1976, 98, 1031;
8. (b) Engler, H.; Taurog, A.; Nakashima, T. Biochem. Pharmacol. 1982, 31, 380.
9. (c) Taurog, A.; Dorris, M. L.; Guziec, F. S. Endocrinology 1989, 124, 30 and references therein;
10. (d) Raby, C.; Lagorce, J. F.; Jambut-Absil, A. C.; Buxeraud, J.; Catanzano, G. Endocrinology 1990, 126, 1683;
11. (e) du Mont, W.-W.; Mugesh, G.; Wismach, C.; Jones, P. Angew. Chem., Int. Ed. 2001, 40, 2486;
12. (d) Carla Aragoni, M.; Area, M.; Demartin, F.; Devillanova, F. A.; Garau, A.; Isaia, F.; Lippolis, V.; Verani, G. J. Am.Chem. Soc. 2002, 124, 4538.
13. Renth, E.O.; Schramm, K.; Anderskewitz, R.; Birke, F.; Fuegner, A.; Heuer, H. German Offen Patent 1994, 4,309,285; Chemical Abstract 1995, 122, 81416c.
14. Reddy, B. S.; Reddy, R. B.; Mouli, G. V. P. C.; Reddy, Y. D. Phosphorus Sulfur and Silicon and the Related Elements, 1991, 63, 143.
15. Foscolos, G. B.; Tsatsas, G.; Costakis, E. Chimika Chronika, 1980, 9, 239.
16. Doble A.; Martin I. L. Trends in Pharmacological Sciences, 1992, 13, 76.
17. Pharmaceutical S. S. Co. Ltd. Jpn Kokai Tokkyo Koho, 1981, 56123992; Chem. Abstr. 1981, 96, 35299.
18. (a) Tierney, J. P.; Lidström, P. Microwave Assisted Organic Synthesis Blackwell: Oxford, 2005;
19. (b) Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250;
20. (c) Kuznetsov, D. V.; Raev, V. A.; Kuranov, G. L.; Arapov, O. V.; Kostikov, R. R. Russ. J. Org. Chem. 2005, 41, 1719;
21. (d) Romanova, N. N.; Gravis, A. G.; Zyk, N. V. Russ. Chem. Rev. 2005, 74, 969;
22. (e) Kappe, C. O. Am. Lab. 2001, 33, 19.
23. El Ashry, E. S. H.; Ramadan, E.; Kassem, A. A.; Hagar, M. Adv. Heterocycl. Chem. 2005, 88, 1.
24. El Ashry, E. S. H.; Kassem, A. A.; Ramadan, E. Adv. Heterocycl. Chem. 2006, 90, 1.
25. El Ashry, E. S. H.; Kassem, A. A. ARKIVOC 2006, ix, 1.
26. Abdel Rahman, A.; El Ashry, E. S. H. Synlett 2002, 2043.
27. Abdel-Hamid, H.; Ramadan, E.; Hagar, M.; El Ashry, E. S. H. Synth. Commun. 2004, 377.
28. El Ashry, E. S. H.; Ramadan, E.; Abdel-Hamid, H.; Hagar, M. Lett. Org. Chem. 2005, 2, 415.
29. El Ashry, E. S. H.; Ramadan, E.; Abdel-Hamid, H.; Hagar M. Synth. Commun. 2005, 35, 2243.
30. El Ashry, E. S. H.; Ramadan, E.; Abdel-Hamid, H.; Hagar, M. J. Chem. Res. 2005, 262.
31. El Ashry, E. S. H., Ramadan, E.; Abdel-Hamid, H.; Hagar, M. Synlett, 2004, 723.
32. El Ashry, E. S. H.; Awad, L. F.; Abdel-Hamid, H.; Atta, I. A. J. Carbohydr. Chem. 2005, 24, 745.
33. El Ashry, E. S. H.; Awad, L. F.; Abdel Hamid, H.; Atta, A. I. Nucleotides Nucleosides Nucelic Acid, 2006, 25, 325.
34. El Ashry, E. S. H.; Awad, L. F.; Abdel-Hamid, H.; Atta, I. A. Int. Soc. For Nucleosides Nucleotides Nucleic acids, XVIInt. Round Table, Minneaoplis, Minnesota, USA, PS. 2004;
35. Nucleosides Nucleotides Nucleic acids, 2005, 24, 427.
36. El Ashry, E. S. H.; Rashed, N.; Awad, L. F.; Ramadan, E.; Abdel-Maggeed, S. M.; Rezki, N. Arkivoc, 2007, vii, 30.
37. El Ashry, E. S. H.; Kassem, A. A.; Abdel-Hamid, H.; Louis, F. F.; Khattab, Sh. A. N.; Aouad, M. R. J. Heterocycl. Chem. 2006, 43, 1.
38. Alper, H.; Keung, E. C. H. J . Org. Chem. 1972, 37, 1464.
39. El Ashry, E. S. H.; Rashed, N.; Awad, L. F.; Ramadan, E.; Abdel-Maggeed, S. M.; Rezki, N. Nucleosides Nucleotides Nucleic acids 2007, 26, 1.
40. Bhatt, M. V.; Lyer, B. H.; Guha, P. C. Current Science 1948, 17, 184.
41. Bhatt, M. V.; Lyer, B. H.; Guha, P. C. J. Ind. Inst. Science 1949, 31A, 43.
42. Abramova, N. D.; Skvortsova, G. G.; Trzhtsinskaya, B. V. Z. Org. Khim. 1984, 20, 2031.
43. Salimi, M.; Amini, M.; Shafiee, A. Phosphorus Sulfur and Silicon and the Related Elements 2005, 180, 1587.
44. Mathew, J.; Purushothaman, E. J. Indian Chem. Soc. 1991, 68, 670.
45. Stewart, J. P. MOPAC, Version 7.00, QCPE program.
46. Merrill, G. N. J. Phy. Org. Chem., 2007, 20, 19.
47. Merrill, G. N. J. Phy. Org. Chem., 2004, 17, 241.
48. Kulig, K.; Nowicki, P.; Malawska, B. Polish J. Chem. 2007, 81, 179.
49. Rezki, N.; Rashed, N.; Awad, L. F.; Ramadan, E.; Abdel-Maggeed, S. M.; El Ashry, E. S. H. Phosphorus Sulfur and Silicon and the Related Elements Submitted for publication.