A novel reaction of 4-(arylmethylene)-2-phenyloxazol-5(4H)-ones with pyridin-2-amine: Formation of 3-(arylmethyl)-3-(benzoylamino)imidazo-[1,2-a] pyridin-2(3H)-ones

Synthesis

Volumn , Issue 4, 2007, Pages 558-564

  Tu, Shujiang ^a   Zhang, Junyong ^a   Jia, Runhong ^a   Zhang, Yan ^a   Jiang, Bo ^a   Shi, Feng ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

3 (arylmethyl) 3 (benzoylamino)imidazo 1,2 a pyridin 2(3H) ones; 4 (arylmethylene) 2 phenyloxazol 5(4H) ones; Cascade reaction; Heterocycles; Microwave irradiation

Indexed keywords

4-(ARYLMETHYLENE)-2-PHENYLOXAZOL-5(4H)- ONES; CASCADE REACTION; HETEROCYCLES;

AMINES; DERIVATIVES; ETHYLENE GLYCOL; MICROWAVES;

ALCOHOLS;

3 (ARYLMETHYL) 3 (BENZOYLAMINO) IMIDAZO [1,2 ALPHA] PRYIDIN 2(3H) ONE DERIVATIVE; 4 (ARYLMETHYLENE) 2 PHENYLOXAZOL 5(4H) ONE DERIVATIVE; AMINE; ETHYLENE GLYCOL; OXAZOLONE; PYRIDIN 2 AMINE; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICROWAVE IRRADIATION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33947528849     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965898     Document Type: Article

References (37)

1. (a) Elhakmaoui, A.; Gueiffier, A.; Milhavet, J.-C.; Blache, Y.; Chapat, J.-P.; Chavignon, O.; Teulade, J.-C.; Snoeck, R.; Andrei, G.; De Clercq, E. Bioorg. Med. Chem. Lett. 1994, 4, 1937.
2. (b) Gueiffier, A.; Lhassani, M.; Elhakmaoui, A.; Snoeck, R.; Andrei, G.; Chavignon, O.; Teulade, J.-C.; Kerbal, A.; Essassi, E. M.; Debouzy, J.-C.; Witvrouw, M.; Blache, Y.; Balzarini, J.; De Clercq, E.; Chapat, J.-P. J. Med. Chem. 1996, 39, 2856.
3. (c) Townsend, L. B.; Drach, J. C. WO 09727205, 1997; Chem. Abstr., 1997, 127, 190983.
4. (d) Gueiffier, A.; Mavel, S.; Lhassani, M.; Elhakmaoui, A.; Snoeck, R.; Andrei, G.; Chavignon, O.; Teulade, J.-C.; Witvrouw, M.; Balzarini, J.; De Clercq, E.; Chapat, J.-P. J. Med. Chem. 1998, 41, 5108.
5. (e) Mavel, S.; Renou, J. L.; Galtier, C.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E.; Gueiffier, A. Arzneim.-Forsch. 2001, 51, 304;
6. Chem. Abstr., 2001, 135, 131730.
7. Teulade, J. C.; Grassy, G.; Girard, J. P.; Chapat, J. P.; de Buochberg, M. M. S. Eur. J. Med. Chem. 1978, 13, 271.
8. (a) Almirante, L.; Polo, L.; Mugnaini, A.; Provinciali, E.; Rugarli, P.; Biancotti, A.; Gamba, A.; Murmann, W. J. Med. Chem. 1965, 8, 305.
9. (b) Abignente, E.; Arena, F.; Luraschi, E.; Saturnino, C.; Rossi, F.; Lampa, E.; Cazzola, M.; Brandinelli, E.; Marrazzo, R.; Marmo, E. Rend. Atti. Accad. Sci. Med. Chir. 1985, 139, 313;
10. Chem. Abstr., 1986, 105, 126822.
11. (c) Abignente, E. Actual. Chim. Ther. 1991, 18, 193,
12. Chem. Abstr., 1991, 115, 256028.
13. Bartholini, G. In Imidazopyridines in Anxiety Disorders; L.E.R.S. Monograph Series, Vol. 8; Raven Press: New York, 1993, 1-5;
14. Chem. Abstr., 1996, 124, 164079.
15. Fuchs, K.; Romig, M.; Mendla, K.; Briem, H.; Fechteler, K. WO 0214313, 2002; Chem. Abstr., 2002, 136, 183824.
16. Abe, Y.; Kayakiri, H.; Satoh, S.; Inoue, T.; Sawada, Y.; Imai, K.; Inamura, N.; Asano, M.; Hatori, C.; Katayama, A.; Oku, T.; Tanaka, H. J. Med. Chem. 1998, 41, 564.
17. Moog, C.; Wick, A.; Le Ber, P.; Kirn, A.; Aubertin, A.-M. Antiviral Res. 1994, 24, 275.
18. Langer, S. Z.; Arbilla, S.; Benavides, J.; Scatton, B. Adv. Biochem. Psychopharmacol. 1990, 46, 61.
19. (a) Hand, E. S.; Paudler, W. W. J. Org. Chem. 1978, 43, 2900.
20. (b) Rydzkowski, R.; Blondeau, D.; Sliwa, H. Tetrahedron Lett. 1985, 26, 2571.
21. (c) Löber, S.; Hübner, H.; Gmeiner, P. Bioorg. Med. Chem. Lett. 1999, 9, 97.
22. (d) Tomoda, H.; Hirano, T.; Saito, S.; Mutai, T.; Araki, K. Bull. Chem. Soc. Jpn. 1999, 72, 1327.
23. (e) Ikemoto, T.; Wakimasu, M. Heterocycles 2001, 55, 99.
24. Hubert, A. J.; Reimlinger, H. Chem. Ber. 1970, 103, 3811.
25. Galons, H.; Bergerat, I.; Combet Farnoux, C.; Miocque, M. Synthesis 1982, 1103.
26. Knölker, H.-J.; Boese, R.; Hitzemann, R. Chem. Ber. 1990, 123, 327.
27. Groziak, M. P.; Wilson, S. R.; Clauson, G. L.; Leonard, N. J. J. Am. Chem. Soc. 1986,108, 8002.
28. Groebke, K.; Weber, L.; Mehlin, F. Synlett 1998, 661.
29. (a) Tu, S.; Fang, F.; Miao, C.; Jiang, H.; Feng, Y.; Shi, D.; Wang, X. Tetrahedron Lett. 2003, 44, 6153.
30. (b) Tu, S.; Fang, F.; Zhu, S.; Li, T.; Zhang, X.; Zhuang, Q. Synlett 2004, 537.
31. (c) Tu, S.; Li, T.; Shi, F.; Wang, Q.; Zhang, J.; Xu, J.; Zhu, X.; Zhang, X.; Zhu, S.; Shi, D. Synthesis 2005, 3045.
32. (d) Tu, S.; Zhang, J.; Zhu, X.; Xu, J.; Zhang, Y.; Wang, Q.; Jia, R.; Jiang, B.; Zhang, J. Bioorg. Med. Chem. Lett. 2006, 16, 3578.
33. (e) Tu, S.; Zhu, X.; Zhang, J.; Xu, J.; Zhang, Y.; Wang, Q.; Jia, R.; Jiang, B.; Zhang, J.; Yao, C. Bioorg. Med. Chem. Lett. 2006, 16, 2925.
34. Tu, S. J.; Jiang, H.; Zhuang, Q. Y.; Miao, C. B.; Shi, D. Q.; Wang, X. S.; Gao, Y. Chin. J. Org. Chem. 2003, 23, 491.
35. Mustafa, A.; Asker, W.; Harhash, A. H.; Khalifa, M. A. E.; Zayed, E. M. Justus Liebigs Ann. Chem. 1968, 713, 151.
36. Vanghelovici, M.; Stefanescu, A. Soc. Chim. Romania, Sect. Soc. romane Stiinte, Bul. Chim. pura apl. 1942, 3A, 159;
37. Chem. Abstr. 1944, 38, 36952.