A facile approach to 4,5-dihydro[1,2,4]triazolo[3,2-d][1,5]benzoxazepines

Synthesis

Volumn , Issue 11, 2007, Pages 1629-1634

  Meng, Qingqing ^a   Bai, Hexiang ^a   Li, Zhiming ^a   Wang, Quanrui ^a   Tao, Fenggang ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

1 aza 2 azoniaallene cations; Benzoxazepine; Cycloaddition; Nitriles; Ring enlargement

Indexed keywords

AZONIAALLENE CATIONS; BENZOXAZEPINE; CRYSTAL DIFFRACTION ANALYSIS; RING ENLARGEMENT;

CYCLOADDITION; DERIVATIVES; DIFFRACTION; MOLECULAR STRUCTURE; POSITIVE IONS; REACTION KINETICS;

AROMATIC COMPOUNDS;

2 BENZYL 4,5 DIHYDRO 8,10 DIMETHYL[1,2,4]TRIAZOLO[3,2 D][1,5]BENZOXAZEPINE; 3 BENZYL 1 (2 HYDROXY 5 METHYL)PHENYL 5 STYRYL 1H 1,2,4 TRIAZOLE; 4,5 DIHYDRO 2,8,10 TRIMETHYL[1,2,4]TRIAZOLO[3,2 D][1,5]BENZOXAZEPINE; 4,5 DIHYDRO 2,9 DIMETHYL 5 PHENYL[1,2,4]TRIAZOLO[3,2 D][1,5]BENZOXAZEPINE; 4,5 DIHYDRO 8,10 DIMETHYL 2 PHENYL[1,2,4]TRIAZOLO[3,2 D][1,5]BENZOXAZEPINE; 4,5 DIHYDRO 9 METHOXY 2 METHYL 5 PHENYL[1,2,4]TRIAZOLO[3,2 D][1,5]BENZOXAZEPINE; 4,5 DIHYDRO 9 METHYL 2 [2 (5 ETHOXYCARBONYL 2 METHOXYPHENOXY)PHENYL] 5 PHENYL[1,2,4]TRIAZOLO[3,2 D][1,5]BENZOXAZEPINE; 4,5 DIHYDRO 9 METHYL 2 [4 (5 ETHOXYCARBONYL 2 METHOXYPHENOXY)PHENYL] 5 PHENYL[1,2,4]TRIAZOLO[3,2 D][1,5]BENZOXAZEPINE; 4,5 DIHYDRO 9 METHYL 5 PHENYL 2 PROPYL[1,2,4]TRIAZOLO[3,2 D][1,5]BENZOXAZEPINE; 4,5 DIHYDRO[1,2,4]TRIAZOLO[3,2 D]BENZOXAZEPINE DERIVATIVE; ACETIC ACID DERIVATIVE; ALUMINUM CHLORIDE; AZOACETATE DERIVATIVE; LEWIS ACID; NITRILE; OXAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CYCLOADDITION; DIPOLE; DRUG STRUCTURE; DRUG SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 34250337719     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-966059     Document Type: Article

References (32)

1. (a) Garofalo, A.; Balconi, G.; Botta, M.; Corelli, F.; D'Incalci, M.; Fabrizi, G.; Fiorini, I.; Lamba, D.; Nacci, V. Eur. J. Med. Chem. 1993, 28, 213.
2. (b) Grunewald, G. L.; Dahanukar, V. H.; Ching, P.; Criscione, K. R. J. Med. Chem. 1996, 39, 3539.
3. (c) Neamati, N.; Trpin, J. A.; Winslow, H. E.; Christensen, J. L.; Williamson, K.; Orr, A.; Rice, W. G.; Pommier, Y.; Garofalo, A.; Brizzi, A.; Campiani, G.; Fiorini, I.; Nacci, V. J. J. Med. Chem. 1999, 42, 3334.
4. (d) Katritzky, A. R.; Xu, Y.-J.; He, H.-Y. J. Chem. Soc., Perkin Trans. 1 2002, 592.
5. (a) Toshiyuki, H.; Takuhiro, I.; Hisao, Y. German Patent 2014223, 1970; Chem. Abstr. 1970, 73, 120697.
6. (b) Standridge, R. T. US Patent 4125538, 1978; Chem. Abstr. 1979, 90, 72246.
7. (a) Steiner, G.; Franke, A.; Hädicke, E.; Lenke, D.; Teschendorf, H.-J.; Hofmann, H.-P.; Kreiskott, H.; Worstmann, W. J. J. Med. Chem. 1986, 29, 1877.
8. (b) O'Neil, I. A.; Murray, C. L.; Hunter, R. C.; Kalindjian, S. B.; Jenkins, T. C. Synlett 1997, 75.
9. (c) Kraus, G. A. US Patent 4545935, 1985; Chem. Abstr. 1986, 104, 148922.
10. Siegl, P. K. S.; Goldberg, A. I.; Goldberg, M. R.; Chang, P. I. US Patent 5817658, 1998; Chem. Abstr. 1998, 129, 290151.
11. (a) Bajaj, K.; Archana Kumar, A. Eur. J. Med. Chem. 2004, 39, 369.
12. (b) Buttero, P. D.; Molteni, G.; Papagnib, A.; Miozzo, L. Tetrahedron: Asymmetry 2004, 15, 2555.
13. (c) Martinez, L. R.; Zarraga, J. G. A.; Duran, M. E.; Apam, M. T. R.; Canas, R. Bioorg. Med. Chem. Lett. 2002, 12, 1675.
14. (d) Kawakami, Y.; Kitani, H.; Yuasa, S.; Abe, M.; Moriwaki, M.; Kagashima, M.; Terasawa, M.; Tahara, T. Eur. J. Med. Chem. 1996, 31, 683.
15. (e) Tanaka, H.; Nakao, T. J. Heterocycl. Chem. 1997, 34, 921.
16. (f) Broggini, G.; Garanti, L.; Molteni, G.; Zecchi, G. Synthesis 1995, 1483.
17. (g) Bartsch, H.; Erker, T. J. Heterocycl. Chem. 1990, 27, 991.
18. For a recent review, see: Bridges, A. J. Chem. Rev. 2001, 101, 2541.
19. Smith, L. II; Piatnitski, E. L.; Kiselyov, A. S.; Ouyang, X.; Chen, X.; Burdzovic-Wizemann, S.; Xu, Y.; Wang, Y.; Rosler, R. L.; Patel, S. N.; Chiang, H.-H.; Milligan, D. L.; Columbus, J.; Wong, W. C.; Doody, J. F.; Hadari, Y. R. Bioorg. Med. Chem. Lett. 2006, 16, 1643.
20. Mc Gee, M. M.; Gemma, S.; Butini, S.; Ramunno, A.; Zisterer, D.; Fattorusso, M.; Catalanotti, C. B.; Kukreja, G.; Fiorini, I.; Pisano, C.; Cucco, C.; Novellino, E.; Nacci, V.; Williams, D. C.; Campiani, G. J. Med. Chem. 2005, 48, 4367; and references cited therein.
21. (a) Liu, X.; Wang, Q.; Liu, Y.; Fan, Y.; Ding, Z. Synthesis 2000, 435.
22. (b) Liu, X.; Liu, Y.; Wang, Q.; Zou, J. Synth. Commun. 2000, 30, 119.
23. (c) Wang, Q.; Liu, X.; Li, F.; Ding, Z.; Tao, F. Synth. Commun. 2002, 32, 1327.
24. (d) Wang, Q.; Li, Z.; Yang, H.; Li, F.; Ding, Z.; Tao, F. Synthesis 2003, 1231.
25. (e) Liu, X.; Liu, Y.; Ding, Z.; Wang, Q.; Zhang, C. J. Heterocycl. Chem. 2000, 37, 287.
26. Meng, Q.; Bai, H.; Wang, Q.; Tao, F. Synthesis 2007, 33.
27. For examples, see: (a) Master, H. E.; Khan, S. I.; Poojari, K. A. Bioorg. Med. Chem. Lett. 2003, 13, 1249.
28. (b) Master, H. E.; Khan, S. I.; Poojari, K. A. Bioorg. Med. Chem. 2005, 13, 4891.
29. (c) Arnold, L. D.; Calderwood, D. J.; Dixon, R. W.; Johnston, D. N.; Kamens, J. S.; Munschauer, R.; Rafferty, P.; Ratnofsky, S. E. Bioorg. Med. Chem. Lett. 2000, 10, 2167.
30. (d) Calderwood, D. J.; Johnston, D. N.; Munschauer, R.; Rafferty, P. Bioorg. Med. Chem. Lett. 2002, 12, 1683.
31. Evans, D.; Lockhart, J. M. J. Chem. Soc. 1965, 4806.
32. Borkhade, K. J.; Marathey, M. G. Indian J. Chem. 1970, 8, 796.