A convenient new synthesis of fused 1,2,4-triazoles: The oxidation of heterocyclic hydrazones using copper dichloride

Tetrahedron

Volumn 61, Issue 24, 2005, Pages 5942-5947

  Ciesielski, Michael ^a   Pufky, Daniela ^a   Döring, Manfred ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

1,2,4 Triazoles; Copper; Hydrazones; Oxidation

Indexed keywords

1 (3,4 DIMETHOXYPHENYL) 1,2,4 TRIAZOLO[4,3 A]QUINOXALINE; 1 (4 CHLOROPHENYL) 1,2,4 TRIAZOLO[4,3 A]PHTHALAZINE; 1 PROPYL 1,2,4 TRIAZOLO[4,3 A]QUINOXALINE; 1,2,4 TRIAZOLE DERIVATIVE; 3 (2 CHLOROPHENYL) 1,2,4 TRIAZOLO[3,4 A]PHTHALAZINE; 3 (2 CHLOROPHENYL) 1,2,4 TRIAZOLO[4,3 A]PYRIDINE; 3 (3,4 DIMETHOXYPHENYL) 1,2,4 TRIAZOLO[4,3 A]PYRIMIDINE; 3 (4 CHLOROPHENYL) 1,2,4 TRIAZOLO[4,3 A]PYRIDINE; 3 (4 CHLOROPHENYL) 1,2,4 TRIAZOLO[4,3 A]PYRIMIDINE; 3 (4 HYDROXYPHENYL) 1,2,4 TRIAZOLO[4,3 A]PYRIDINE; 3 (4 NITROPHENYL) 1,2,4 TRIAZOLO[4,3 A]PYRIDINE; 5,7,9 TRIMETHYL 3 PROPYL 5,9 DIHYDRO 6H 1,2,4 TRIAZOLO[4,3 E]PURINE 6,8(7H) DIONE; 6 CHLORO 3 (3,4 DIMETHOXYPHENYL) 1,2,4 TRIAZOLO[4,3 B]PYRIDAZINE; 6 CHLORO 3 (4 CHLOROPHENYL) 1,2,4 TRIAZOLO[4,3 B]PYRIDAZINE; COPPER CHLORIDE; COPPER DICHLORIDE; FUSED HETEROCYCLIC RINGS; HYDRAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; MOLECULE; OXIDATION; PHASE TRANSITION; PRIORITY JOURNAL; QUANTUM YIELD;

EID: 19744369316     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.111     Document Type: Article

References (25)

1. S.A. El-Hawash, N.S. Habib, and N.H. Fanaki Pharmazie 54 1999 808 813
2. D.J. Brown, and Y. Iwai Aust. J. Chem. 32 1979 2727 2733
3. G. Tarzia, E. Ocelli, E. Toja, D. Barone, N. Corsico, L. Gallico, and F. Luzzani J. Med. Chem. 31 1988 1115 1123
4. Trust, R. I.; Albright, J.D. U.S. Patent 4 242 515, 1980.
5. G. Tarzia, E. Ocelli, and D. Barone Il Farmaco 44 1989 3 16
6. Peignier, R., Chêne, A., Cantregril, R., Mortier, J. Eur. Patent 441718. ; Chem. Abstr. 1991 115 208000.
7. Cantegril, R., Chêne, A., Mortier, J., Peignier, R. Eur. Patent 483027.; Chem. Abstr. 1992 117 131214.
8. S. Sarges, H.R. Howard, R.G. Browne, L.A. Lebel, P.A. Seymour, and B.K. Koe J. Med. Chem. 33 1990 2240 2254
9. J.D. Bower, and F.P. Doyle J. Chem. Soc. 1957 727 732
10. A. Pollak, and M. Tišler Tetrahedron 22 1966 2073 2079
11. M.S. Gibson Tetrahedron 19 1963 1587 1589
12. P. Bourgeois, R. Cantegril, A. Chêne, J. Gelin, J. Mortier, and J. Moyroud Synth. Comm. 23 1993 3195 3199
13. A.K. Sadana, Y. Mirza, K.R. Aneja, and O. Prakash Eur. J. Med. Chem. 38 2003 533 536
14. D. Kumar, V.G. Kondapalli, S. Chandra, D. Harmeet, S.R. Vajja, and S. Rajender Green Chem. 6 2004 156 157
15. S. Crljenak, I. Tabaković, D. Jeremić, and I. Gaon Acta Chem. Scand. B37 1983 527 535
16. M.E. Bluhm, M. Ciesielski, H. Görls, and M. Döring Angew. Chem., Int. Ed. 41 2002 2962 2965
17. M.E. Bluhm, M. Ciesielski, H. Görls, and M. Döring Angew. Chem. 114 2002 3104 3107
18. M.E. Bluhm, M. Ciesielski, W. Görls, O. Walter, and M. Döring Inorg. Chem. 2003 8878 8885
19. S. Naqui, and V.R. Srinivasan Indian J. Chem. 3 1965 162 164
20. T. Tsujikawa, and M. Tatsuta Chem. Pharm. Bull. 25 1977 3137 3146
21. D.J. Brown, and T. Namagatsu Aust. J. Chem. 30 1977 2515 2524
22. A. Pollak, and M. Tisler Tetrahedron 22 1966 2073 2079
23. D. Shiho, and S.J. Tagami Am. Chem. Soc. 82 1960 4044 4054
24. A.R. Todeschini, A.L.P de Miranda, K.C.da Silva, S.C. Parrini, and E.J. Barreiro Eur. J. Med. Chem. Chim. Ther. 33 1998 189 200
25. Klosa J. Chem. Ber. 93 1955 211 217