Quantum-chemical studies of the nitration of benzazoles

Arkivoc

Volumn 2005, Issue 9, 2005, Pages 80-89

  Breza, Martin ^a   Milata, Viktor ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

Author keywords

1 methylbenzimidazole; Benzimidazole; Benzotriazole; N methylbenzotriazole; Nitration

Indexed keywords

4 NITRO 1 METHYLBENZOTRIAZOLE; 4 NITRO 2 FORMYLAMINOPHENOL; 4 NITRO 2 METHYLBENZOTRIAZOLE; 4 NITRO 2,1,3 BENZSELENADIAZOLE; 4 NITRO 2,1,3 BENZTHIADIAZOLE; 4(7) NITROBENZOTRIAZOLE; 5 NITRO 1 METHYLBENZIMIDAZOLE; 5 NITRO 2 FORMYLAMINOPHENOL; 5 NITRO 2 METHYLBENZOTRIAZOLE; 5 NITRO 2,1,3 BENZTHIADIAZOLE; 5(6) NITRO 2 BENZIMIDAZOLONE; 5(6) NITROBENZIMIDAZOLE; 6 NITRO 1 METHYLBENZIMIDAZOLE; 6 NITRO 2 PHENYLBENZOXAZOLE; 7 NITRO 1 METHYLBENZOTRIAZOLE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; NITRATION; QUANTUM CHEMISTRY;

EID: 15444372478     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (54)

1. Elguero, J.; Marzin, C.; Katritzky, A.R.; Linda, P. The Tautomerism of Heterocycles, Academic Press, New York 1976.
2. Katritzky, A.R.; Karelson, M.; Harris, P.A. Heterocycles, 1991, 32, 329.
3. Advances in Heterocyclic Chemistry, Vol. 76, ed. Katritzky A.R., Academic Press, San Diego 2000.
4. Hudlicky, M. Reductions in Organic Chemistry, Ellis Horwood Ltd., Chichester 1984.
5. Murashima, T.; Fujita, K.; Ono, K.; Ogawa, T.; Uno, H.; Ono, N. J. Chem. Soc. Perkin Trans. 1, 1996, 1403.
6. Vats, S.; Stuttard, C.; Vining, L.C. J. Bacteriol. 1987, 169, 3809.
7. Kirner, S.; van Pée, K.-H. Angew. Chem. Int. Ed. Engl. 1994, 33, 352.
8. Adams, G.E.; Stratford, I.J. Biochem. Pharmacol. 1986, 35, 71.
9. Denny, W.A.; Atwell, G.J.; Roberts, P.B.; Anderson, R.F.; Boyd, M.; Lock, C.J.L.; Wilson, W.R. J. Med. Chem. 1992, 35, 4832.
10. Narita, S.; Kitagawa, T. Chem. Pharm. Bull. 1989, 37, 1005.
11. Narita, S.; Tasaki, T.; Kitagawa, T. Chem. Pharm. Bull. 1989, 37, 1009.
12. Llinares, J.; Galy, J.-P.; Faure, R.; Vincent, E.-J.; Elguero, J. Can. J. Chem. 1979, 57, 937.
13. Khaleckij, A. M.; Pesin, B. G. Zh. Obsch. Khim. 1950, 20, 1914.
14. Komin, A. P.; Carmack, M. J. Heterocycl. Chem. 1975, 12, 829.
15. Tomas, F.; Catalan, J.; Perez, P.; Elguero J. J. Org. Chem. 1994, 59, 2799.
16. Palmer, M.H.; Kurshid, M.M.P.; Rayner, T.J.; Smith, J.A.S. Chem. Phys. 1994, 182, 27.
17. Fischer, G.; Cao, X.L.; Purchase, R.L. Chem. Phys. Lett. 1996, 262, 689.
18. Negri, F.; Caminati, W. Chem. Phys. Lett. 1996, 260, 119.
19. Bigotto, A.; Pandey, A.N.; Zerbo, C. Spectroscopy Lett. 1996, 29, 511.
20. Schoone, K.; Smets, J.; Houben, L.; Van Bael, M.K.; Adamowicz, L.; Maes, G. J. Phys. Chem. A, 1998, 102, 4863.
21. Roth, W.; Jacoby, C.; Westphal, A.; Schmitt, M. J. Phys. Chem. A, 1998, 102, 3048.
22. Barsky, D.; Kool, E.T.; Colvin, M.E. J. Biomol. Struct. Dynam. 1999, 16, 1119.
23. Torrent, M.; Musaev, D.G.; Morokuma, K.; Ke S.C.; Warncke, K. J. Phys. Chem. B, 1999, 103, 8618.
24. Roth, W.; Spangenberg, D.; Janzen, C.; Westphal, A.; Schmitt, M. Chem. Phys. 1999, 248, 17.
25. Rademacher, P.; Kowski, K.; Katritzky, A.R.; Denisenko, S.N. J. Mol. Struct. 1999, 513, 47.
26. Jacoby, C.; Roth, W.; Schmitt, M. Appl. Phys. B, 2000, 71, 643.
27. Serrano-Andres, L.; Borin, A.C. Chem. Phys. 2000, 262, 267.
28. Borin, A.C.; Serrano-Andres, L. Chem. Phys. 2000, 262, 253.
29. Wang, H.; Burda, C.; Persy, G.; Wirz, J. J. Am. Chem. Soc. 2000, 122, 5849.
30. Schmitt, M.; Plutzer, C.; Kleinermanns, K. Phys. Chem. Chem. Phys. 2001, 3, 4218.
31. Morsy, M.A.; Al-Khaldi, M.A.; Suwaiyan, A. J. Phys. Chem. A, 2002, 106, 9196.
32. Jagerovic, N.; Jimeno, M.L.; Alkorta, I.; Elguero, J.; Claramunt, R.M. Tetrahedron 2002, 58, 9089.
33. Wiench, J.W.; Koprowski, M.; Stefaniak, L.; Webb, G.A. Polish J. Chem. 2002, 76, 525.
34. Ueno, L.T.; Ribeiro, R.O.; Rocha, M.S.; Suarez-Iha, M.E.V.; Iha, K.; Machado, F.B.C. J. Mol. Struct. (Theochem), 2003, 664, 207.
35. Ludwig, V.; Coutinho, K.; Borin, A.C.; Canuto, S. Int. J. Quant. Chem. 2003, 95, 572.
36. Borin, A.C.; Serrano-Andres, L.; Ludwig, V.; Canuto, S. Phys. Chem. Chem. Phys. 2004, 3, 353.
37. Fowler, P.W.; Soncini, A. Polycycl. Arom. Compds. 2004, 24, 353.
38. Brown, R.D.; Heffernan, M.L. J. Chem. Soc. 1956, 4288.
39. McHugh, C.J.; Tackley, D.R.; Graham, D. Heterocycles 2002, 57, 1461.
40. Fukui, K.; Yonezawa, T.; Nagata, Ch.; Shingu, H. J. Chem. Phys. 1954, 22, 1433.
41. Schellhammer, C.W.; Schroeder, J.; Joop, N. Tetrahedron 1970, 26, 497.
42. Ambacheu, K.D.; Pleshakov, V.G.; Baatkh, B.S.; Zvolinskii, M.D.; Kharlamova, M.D.; Obynochnyi, A.A.; Prostakov, N.S. Chem. Heterocycl. Compds. 2000, 36, 421.
43. Bamberger, E.; Berlé, B. Ann. 1893, 273, 340.
44. Fischer, O.; Hess, W. Ber. 1903, 36, 3968.
45. Milata, V.; Ilavský, D. Bull. Soc. Chim. Belg. 1996, 105, 213.
46. Fries, K.; Güterbock, H.; Kühn, H. Justus Liebigs Ann. Chem. 1934, 511, 229.
47. Stephens, F. F.; Bower, D. Jr. J. Chem. Soc. 1949, 2971.
48. Ward, E.R.; Poesche, W.H. J. Chem. Soc. 1961, 2825.
49. Sawicki, E.; Carr A. J. Org. Chem. 1957, 22, 503.
50. Wiley, H.R.; Hussung, K.F. J. Am. Chem. Soc. 1957, 79, 4395.
51. Kamel, M.; Sherif, S.; Kamel, M.M. Tetrahedron 1964, 20, 211.
52. Schindlbauer, H.; Kwiecinski W. Monatsh. Chem. 1976, 107, 1307.
53. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Montgomery, J.A. Jr.; Vreven, T.; Kudin, K.N.; Burant, J.C.; Millam, J.M.; Iyengar, S.S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G.A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H.P.; Cross, J.B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P.Y.; Morokuma, K.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Zakrzewski, V.G.; Dapprich, S.; Daniels, A.D.; Strain, M.C.; Farkas, O.; Malick, D. K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Ortiz, J.V.; Cui, Q.; Baboul, A.G.; Clifford, S.; Cioslowski, J.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.1, Gaussian, Inc., Pittsburgh PA 2003.
54. Woon D.E., Dunning T.H., Jr. J. Chem. Phys. 1993, 98, 1358.