An efficient one-pot, four-component synthesis of {[(1H-1,2,3-Triazol-4-yl) methoxy]phenyl}-1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives

Helvetica Chimica Acta

Volumn 94, Issue 8, 2011, Pages 1416-1425

  Torkian, Laleh ^a   Dabiri, Minoo ^a   Salehi, Peyman ^a   Bararjanian, Morteza ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Active methylene compounds; Imidazolium trifluoroacetate, 1 methyl ; Multicomponent reactions; Phthalazine 5,10 dione derivatives; Phthalohydrazide; Propargyloxy aldehydes

Indexed keywords

ACTIVE METHYLENE COMPOUNDS; IMIDAZOLIUM; MULTICOMPONENT REACTIONS; PHTHALAZINE-5,10-DIONE DERIVATIVES; PHTHALOHYDRAZIDE; PROPARGYLOXY ALDEHYDES;

ALDEHYDES; SODIUM; SYNTHESIS (CHEMICAL);

CONDENSATION REACTIONS;

3 AMINO 1 [2 [[1 (4 CHLOROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]5 NITROPHENYL] 5,10 DIHYDRO 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CAROBNITRILE; 3 AMINO 1 [4 [[1 (4 CHLOROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY] 3 ETHOXYPHENYL] 5,10 DIHYDRO 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBONITRILE; 3 AMINO 1 [5 BROMO 2 [[1 (3 NITROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]PHENYL] 5,10 DIHYDRO 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBONITRILE; 3 AMINO 5,10 DIHYDRO 1 [2 [[1 (3 NITROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]PHENYL] 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAINE 2 CARBONITRILE; 3 AMINO 5,10 DIHYDRO 1 [2 [[1 (4 NITROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHYOXY]PHENYL] 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAINE 2 CARBONITRILE; 3 AMINO 5,10 DIHYDRO 1 [4 [[1 (4 NITROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]PHENYL] 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBONITRILE; 3 AMINO 5,10 DIHYDRO 1 [5 NITRO 2 [[1 (3 NITROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]PHENYL] 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBONITRILE; 3 AMINO 5,10 DIHYDRO 1 [5 NITRO 2 [[1 (PHENYLMETHYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]PHENY] 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBONITRILE; ETHYL 3 AMINO 1 [2 [[1 (3 FLUOROPHENYL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]PHENYL] 5,10 DIHYDRO 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBOXYLATE; ETHYL 3 AMINO 1 [3 ETHOXY 4 [[1 (PHENYLMETHYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]PHENYL] 5,10 DIHYDRO 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBOXYLATE; ETHYL 3 AMINO 1 [5 BROMO 2 [[1 (PHENYLMETHYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]PHENYL] 5,10 DIHYDRO 5,10 DIOXO 1H PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBOXYLATE; ETHYL 3 AMINO 1 [5 BROMO 2 [[1 [(3 FLUOROPHENYL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]PHENYL] 5,10 DIHYDRO 5,10 1H PYRAZOLO[1,2 B]PHTHALAINE 2 CARBOXYLATE; ETHYL 3 AMINO 5,10 DIHYDRO 1 [2 [[1 (4 NITROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]PHENYL] 5,10 DIOXO HH PYRAZOLO[1,2 B]PHTHALAZINE 2 CARBOXYLATE; ETHYL 3 AMINO 5,10 DIHYDRO 1 [5 NITRO 2 [[1 (4 NITROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]PHENYL] 5,10 DIOXO 1H PYRAOLO[1,2 B]PHTHALAZINE 2 CARBOXYLATE; PHTHALAZINE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ONE POT SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL;

EID: 80051896635     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201000428     Document Type: Article

References (51)

1. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem., Int. Ed. 2001, 40, 2004.
2. J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev. 2007, 36, 1249.
3. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057
4. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem., Int. Ed. 2002, 41, 2596.
5. H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2004, 8, 1128.
6. Y. M. Chabre, R. Roy, Curr. Top. Med. Chem. 2008, 8, 1237
7. M. Colombo, I. Peretto, Drug Discovery Today 2008, 13, 677
8. R. Hanselmann, G. E. Job, G. Johnson, R. L. Lou, J. G. Martynow, M. M. Reeve, Org. Process Res. Dev. 2010, 14, 152
9. R. Moumne, V. Larue, B. Seijo, T. Lecourt, L. Micouin, C. Tisne, Org. Biomol. Chem. 2010, 8, 1154.
10. H. M. Li, F. O. Cheng, A. M. Duft, A. Adronov, J. Am. Chem. Soc. 2005, 127, 14518
11. D. I. Rozkiewicz, D. Janczewski, W. Verboom, B. J. Ravoo, D. N. Reinhoudt, Angew. Chem., Int. Ed. 2006, 45, 5292
12. M. Wyszogrodzka, R. Haag, Chem.-Eur. J. 2008, 14, 9202
13. T. Gadzikwa, O. K. Farha, C. D. Malliakas, M. G. Kanatzidis, J. T. Hupp, S. T. Nguyen, J. Am. Chem. Soc. 2009, 131, 13613
14. P. L. Golas, K. Matyjaszewski, Chem. Soc. Rev. 2010, 39, 1338.
15. M. E. Hahn, T. W. Muir, Trends Biochem. Sci. 2005, 30, 26
16. W. P. Heal, S. R. Wickramasinghe, R. J. Leatherbarrow, E. W. Tate, Org. Biomol. Chem. 2008, 6, 2308
17. M. Ahsanullah, P. Schmieder, R. Kuhne, J. Rademann, Angew. Chem., Int. Ed. 2009, 48, 5042
18. G. Schneider, Nat. Rev. Drug Discovery 2010, 9, 273.
19. R. Alvarez, S. Velazquez, A. SanFelix, S. Aquaro, E. DeClercq, C. F. Perno, A. Karlsson, J. Balzarini, M. J. Camarasa, J. Med. Chem. 1994, 37, 4185.
20. D. R. Buckle, C. J. M. Rockell, H. Smith, B. A. Spicer, J. Med. Chem. 1986, 29, 2262.
21. C. B. Vicentini, V. Brandolini, M. Guarneri, P. Giori, Farmaco 1992, 47, 1021
22. J. C. Fung-Tomc, E. Huczko, B. Minassian, D. P. Bonner, Antimicrob. Agents Chemother. 1998, 42, 313.
23. M. J. Genin, D. A. Allwine, D. J. Anderson, M. R. Barbachyn, D. E. Emmert, S. A. Garmon, D. R. Graber, K. C. Grega, J. B. Hester, D. K. Hutchinson, J. Morris, R. J. Reischer, C. W. Ford, G. E. Zurenko, J. C. Hamel, R. D. Schaadt, D. Stapert, B. H. Yagi, J. Med. Chem. 2000, 43, 953.
24. Y. Naito, F. Akahoshi, S. Takeda, T. Okada, M. Kajii, H. Nishimura, M. Sugiura, C. Fukaya, Y. Kagitani, J. Med. Chem. 1996, 39, 3019.
25. O. Makabe, H. Suzuki, S. Umezawa, Bull. Chem. Soc. Jpn. 1977, 50, 2689.
26. L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137
27. Angew. Chem., Int. Ed. 1993, 32, 131
28. L. F. Tietze, Chem. Rev. 1996, 96, 115
29. L. F. Tietze, T. H. Evers, E. Topken, Angew. Chem. 2001, 113, 927
30. Angew. Chem., Int. Ed. 2001, 40, 903
31. S. Ikeda, Angew. Chem. 2003, 115, 5276
32. Angew. Chem., Int. Ed. 2003, 42, 5120
33. R. J. Linderman, S. Binet, S. R. Petrich, J. Org. Chem. 1999, 64, 336
34. P. Satymaheshwar, S. Jayakumar, J. J. Tepe, Org. Lett. 2002, 4, 3533.
35. J. Zhu, H. Bienaymeh, 'Multicomponent Reaction', Wiley-VCH; Weinheim, 2005.
36. D. B. Ramachary, C. F. Barbas III, Chem.-Eur. J. 2004, 10, 5323.
37. I. Akritopoulou-Zanze, V. Gracias, S. W. Djuric, Tetrahedron Lett. 2004, 45, 8439.
38. V. Gracias, D. Darczak, A. F. Gasiecki, S. W. Djuric, Tetrahedron Lett. 2005, 46, 9053.
39. B. Khanetskyy, D. Dallinger, C. O. Kappe, J. Comb. Chem. 2004, 6, 884.
40. M. Dabiri, P. Salehi, M. Bahramnejad, F. Sherafat, J. Comb. Chem. 2010, 12, 638.
41. N. K. Terrett, A. S. Bell, D. Brown, P. Ellis, Bioorg. Med. Chem. Lett. 1996, 6, 1819.
42. J. Elguero, in 'Comprehensive Heterocyclic Chemistry II', Vol.3, Eds. A.R. Katritzky, C.W. Rees, E.F. Scriven, Elsevier, Oxford, 1996, pp.1-75.
43. S. K. Singh, P. G. Reddy, K. S. Rao, B. B. Lohray, P. Misra, S. A. Rajjak, Y. K. Rao, A. Venkatewarlu, Bioorg. Med. Chem. Lett. 2004, 14, 499.
44. M. J. Genin, C. Biles, B. J. Keiser, S. M. Poppe, S. M. Swaney, W. G. Tarpley, Y. Yagi, D. L. Romero, J. Med. Chem. 2000, 43, 1034.
45. F. Al'-Assar, K. N. Zelenin, E. E. Lesiovskaya, I. P. Bezhan, B. A. Chakchir, Pharm. Chem. J. 2002, 36, 598.
46. R. Ghahremanzadeh, G. I. Shakibaei, A. Bazgir, Synlett 2008, 1129
47. M. Sayyafi, M. Seyyedhamzeh, H. R. Khavasi, A. Bazgir, Tetrahedron 2008, 64, 2375
48. M. R. Nabid, S. J. T. Rezaei, R. Ghahremanzadeh, A. Bazgir, Ultrason. Sonochem. 2010, 17, 159.
49. P. Salehi, M. Dabiri, M. A. Zolfigol, M. A. Bodaghi Fard, Tetrahedron Lett. 2003, 44, 2889
50. M. Dabiri, A. S. Delbari, A. Bazgir, Synlett 2007, 821
51. P. Salehi, M. Dabiri, M. A. Zolfigol, S. Otokesh, M. Baghbanzadeh, Tetrahedron Lett. 2006, 47, 2557.