Base catalyzed synthesis of novel fused-imidazoles from N-Vinyl-1H-imidazole

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 60, Issue 1, 2005, Pages 106-112

  Aly, Ashraf A ^a  

^a El Minia University ^*  (Egypt)

Author keywords

Base Catalysis; Fused Imidazoles; N Vinyl 1H imidazole; Deficients

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; KETONES;

2 ,3-DICHLORO-1 ,4-NAPHTHOQUINONE; 2 ,3-DICHLORO-5 ,6-DICYANO-1 ,4-BENZOQUINONE; BASE CATALYSIS; BASIC CONDITIONS; DIMETHYL ACETYLENEDICARBOXYLATE; FUSED-IMIDAZOLES; NAPHTHOQUINONE; REACTION CONDITIONS;

PLANTS (BOTANY);

1,1,2,2 TETRACYANOETHYLENE; 2 DICYANOMETHYLENEINDANE 1,3 DIONE; 2,3 DICHLORO 1,4 NAPHTHOQUINONE; 2,3 DICHLORO 5,6 DICYANO 1,4 BENZOQUINONE; 2,3 DICYANO 1,4 NAPHTHOQUINONE; 3,4,5,6 TETRACHLORO 1,2 BENZOQUINONE; AZEPINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CHLORANIL; ETHYLENE DERIVATIVE; IMIDAZOLE DERIVATIVE; INDANYLIMIDAZOLO[1,2 A]AZEPINE; ISOQUINOLINE DERIVATIVE; N VINYL 1H IMIDAZOLE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL REACTION; DIELS ALDER REACTION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 13844253541     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2005-0116     Document Type: Article

References (38)

1. J. Sepúlveda-Arques, B. Abarca-González, M. Medio-Simón, Adv. Heterocyclc. Chem. 63, 339 (1995).
2. Y. Chen, V. Raika-Dias, C. J. Lovely, Tetrahedron Lett. 44, 1379 (2003).
3. K. H. Wu, T. C. Chang, Y. T. Wang, Y. S. Hong, T. S. Wu, Eur. Poly. J. 39, 239 (2003).
4. C. Luca, S. Mihailescu, M. Popa, Eur. Poly. J. 38, 1501 (2002).
5. C. Alexander, L. Davidson, W. Hayes, Tetrahedron 59, 2025 (2003).
6. a) N. Pekel, H. Savas, O. Guven, Colloid & Poly. Science 280, 46 (2002);
7. b) N. Pekel, B. Salih, O. Guven, J. Mol. Catalysis B. 21, 273 (2003).
8. C. J. Lovely, H. Du, H. V. Dias, Org. Lett. 3, 1319 (2001).
9. K. Choji, T. Atsushi, T. Tadakuni, J. Heterocycl. Chem. 21, 201 (1984).
10. D. Branowska, A. Rykowski, Synlett. 11, 1892 (2002).
11. B. A. Trofimov, L. V. Morozova, M. V. Sigalov, A. I. Mikhaleva, M. V. Markova, Makromol. Chem. 188, 2251 (1987).
12. K. W. Kottsieper, O. Stelzer, P. Wasserschei, J. Mol. Cat. A. 175, 285 (2001).
13. T. Itoh, M. Miyazaki, K. Negata, A. Ohswa, Tetrahedron 56, 4383 (2000).
14. a) J. Suwinski, W. Szczepankiewicz, Polish J. Chem. 65, 515 (1991);
15. b) J. Suwinski, W. Sczepankiewicz, Tetrahedron Asymm. 2, 941 (1991);
16. c) J. Suwinski, W. Szczepankiewicz, E. M. Holt, Tetrahedron 52, 14905 (1996);
17. d) W. Szczepankiewicz, J. Suwinski, Tetrahedron Lett. 39, 1785 (1998);
18. e) W. Szczepankiewicz, J. Suwinski, Tetrahedron 56, 9343 (2000);
19. f) S. Krompiec, M. Pigulla, W. Szczepankiewicz, T. Bieg, N. Kuznik, K. Leszczynska-Sejda, M. Kubicki, T. Borowiak, Tetrahedron Lett. 42, 7095 (2001);
20. g) J. Suwinski, W. Szczepankiewicz, K. Swierczek, P. Wagner, K. Walczak, Eur. J. Org. Chem. 1080 (2003).
21. C. G. Frost, P. Mendonca, J. Chem. Soc. Perkin Trans. I 2615 (1998).
22. A. A. Aly, N. K. Mohamed, A. A. Hassan, A. E. Mourad, Tetrahedron 55, 1111 (1999).
23. A. A. Aly, A. E. Mourad, K. M. El-Shaieb, H. Hopf, Synth. Commun. 31, 637 (2001).
24. A. A. Aly, H. Hopf, L. Ernst, Eur. J. Org. Chem. 3021 (2000).
25. A. A. Aly, Tetrahedron 59, 6067 (2003).
26. A. A. Aly, Tetrahedron 59, 1739 (2003).
27. A. A. Aly, Org. Biomol. Chem. 1, 756 (2003).
28. A. A. Aly, A. E. Mourad, A. A. Hassan, N. K. Mohamed, B. A. Ali, M. M. El-Sayed, Arch. Pharm. Pharm. Med. Chem. 337, 133 (2004).
29. A. A. Aly, K. M. El-Shaieb, Tetrahedron 60, 3797 (2004).
30. K. Hanazaki, P. Gupta, S. K. Singh, T. Srinivasan, B. Kundu, Geir Hetland, Current Med. Chem.-Anti-Infective Agents 2, 103 (2003).
31. K. Bleicher, F. Gerber, Y. Wüthrich, A. Alanine, and A. Capretta, Tetrahedron Lett. 43, 7687 (2002).
32. N. L. Allinger, MM2 (91) force field Program, obtained from Quantum Chemistry Program, Indiana University; Molecular Mechanics PM3 Program (ACD/3D), Advanced Chemical Development Inc., Toronto, Canada (1988).
33. Chatterjee, S. J. Chem. Soc. B. 725 (1969).
34. M. L. Budni, E. S. Jayadevappa, Spectrochim. Acta. 44A, 607 (1988).
35. R. Grigg, T. Mongkolaussavaratana, J. Chem. Soc. Perkin Trans. I 541 (1988).
36. Siberdt, J. Nasielski, Bull. Soc. Chim. Belg. 106, 29 (1997).
37. A. Diáz-Ortiz; J. R. Carrillo, E. Diez-Barra, A. De la Hoz, M. J. Gomez-Escalonilla, A. Moreno, F. Langa, Tetrahedron 52, 9237 (1996).
38. B. Dolensky, K. Kirk, J. Org. Chem. 66, 4687 (2001).