Iodine-catalyzed synthesis of 2-arylpyrazolo[5,1-b]quinazolin-9(3H)-one derivatives in ionic liquids via domino reaction

Tetrahedron

Volumn 70, Issue 21, 2014, Pages 3440-3446

  Zhou, Yu Jing ^a   Zhang, Mei Mei ^a   Li, Yu Ling ^a   Liu, Yun ^a   Wang, Xiang Shan ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

Domino reaction; Iodine; Pyrazoloquinazoline; Synthesis

Indexed keywords

2 AMINO N' (1 ARYLETHYLIDENE) BENZOHYDRAZIDE; 2 ARYLPYRAZOLO [5,1 B] QUINAZOLIN 9(3H) ONE DERIVATIVE; 2(3 CHLOROPHENYL) 3 METHYLPYRAZOLO [5,1 B] QUINAZOLIN 9(4H) ONE; 2(4 CHLOROPHENYL) 3 METHYLPYRAZOLO [5,1 B] QUINAZOLIN 9(4H) ONE; 2(4 CHLOROPHENYL) 3 PROPYLPYRAZOLO [5,1 B] QUINAZOLIN 9(4H) ONE; 2(4 FLUOROPHENYL) 3 METHYLPYRAZOLO [5,1 B] QUINAZOLIN 9(4H) ONE; 2(4 METHOXYPHENYL) 3 METHYLPYRAZOLO [5,1 B]QUINAZOLIN 9(4H) ONE; 2(4 TOLYL) PYRAZOLO [5,1 B] QUINAZOLIN 9(4H) ONE; 3 ETHYL 7 METHYL 2 PHENYLPYRAZOLO [5,1 B] QUINAZOLIN 9(4H) ONE; 3 METHYL 2 PHENYLPYRAZOLO [5,1 B] QUINAZOLIN 9(4H) ONE; 3 METHYL 2(4 TOLYL) PYRAZOLO [5,1 B] QUINAZOLIN 9(4H) ONE; 3ALPHA 4 DIHYDRO 2 ARYLPYRAZOLO [5,1 B] QUINAZOLIN 9(3H) ONE DERIVATIVE; 7 BROMO 2 PHENYL 3 PROPYLPYRAZOLO [5,1 B] QUINAZOLIN 9(4H) ONE; FORMIC ACID; HYDRAZIDE DERIVATIVE; IODINE; IONIC LIQUID; PYRAZOLE DERIVATIVE; QUINAZOLINE DERIVATIVE; TRIETHYL ORTHOFORMATE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; DOMINO REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ONE POT SYNTHESIS; OXIDATION; PRIORITY JOURNAL;

EID: 84899435273     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.03.075     Document Type: Article

References (30)

1. A. Colquhoun, G.M. Lawrance, I.L. Shamovsky, R.J. Riopelle, and G.M. Ross J. Pharmacol. Exp. Ther. 310 2004 505 511
2. F.F. Hefti, A. Rosenthal, P.A. Walicke, S. Wyatt, G. Vergara, D.L. Shelton, and A.M. Davies Trends Pharmacol. Sci. 27 2006 85 91
3. K. Spiegel, D. Agrafiotis, B. Caprathe, R.E. Davis, M.R. Dickerson, J.H. Fergus, T.W. Hepburn, J.S. Marks, and M. Van Dorf Biochem. Biophys. Res. Commun. 217 1995 488 494
4. J.C. Jaen, E. Laborde, R.A. Bucsh, B.W. Caprathe, R.J. Sorenson, J. Fergus, K. Spiegel, J. Marks, M.R. Dickerson, and R.E. Davis J. Med. Chem. 38 1995 4439 4445
5. Kehler, J.; Ritzen, A.; Langgaard, M.; Nielsen, J.; Farah, M.; Leth-Petersen, S.; Kilburn, J. P. Preparation of pyrazoloquinazoline derivatives and analogs for use as PDE10A enzyme inhibitors. PCT Int. Appl. WO 2012007006 A1 20120119, 2012.
6. M. Caldarelli, M. Angiolini, T. Disingrini, D. Donati, M. Guanci, S. Nuvoloni, H. Posteri, F. Quartieri, M. Silvagni, and R. Colombo Bioorg. Med. Chem. Lett. 21 2011 4507 4511
7. B. Asproni, G. Murineddu, A. Pau, G.A. Pinna, M. Langgard, C.T. Christoffersen, J. Nielsen, and J. Kehler Bioorg. Med. Chem. 19 2011 642 649
8. M. Angiolini, P. Banfi, E. Casale, F. Casuscelli, C. Fiorelli, M.B. Saccardo, M. Silvagni, and F. Zuccotto Bioorg. Med. Chem. Lett. 20 2010 4095 4099
9. I. Beria, D. Ballinari, J.A. Bertrand, D. Borghi, R.T. Bossi, M.G. Brasca, P. Cappella, M. Caruso, W. Ceccarelli, and A. Ciavolella J. Med. Chem. 53 2010 3532 3551
10. Casuscelli, F.; Piutti, C.; Ermoli, A.; Faiardi, D. Preparation of substituted pyrazolo[4,3-h]quinazoline derivatives as kinase inhibitors. PCT Int. Appl. WO 2012080990 A1 20120621, 2012.
11. Ciomei, M.; Scaburri, A. Cdk inhibitor for the treatment of mesothelioma. PCT Int. Appl. WO 2010058006 A1 20100527, 2010.
12. V.A. Chebanov, V.E. Saraev, S.M. Desenko, V.N. Chernenko, I.V. Knyazeva, U. Groth, T.N. Glasnov, and C.O. Kappe J. Org. Chem. 73 2008 5110 5118
13. X.-J. Yang, J.-T. Liu, and H.-J. Lu Tetrahedron 60 2004 2897 2902
14. T.E. Vasquez Jr., T. Nixey, B. Chenera, V. Gore, M.D. Bartberger, Y. Sun, and C. Hulme Mol. Divers. 7 2003 161 164
15. K.U. Sadek, R.A. Mekheimer, T.M. Mohamed, M.S. Moustafa, and M.H. Elnagdi Beilstein J. Org. Chem. 8 2012 18 24
16. V.V. Lipson, N.V. Svetlichnaya, V.V. Borodina, M.G. Shirobokova, S.V. Shishkina, O.V. Shishkin, and V.I. Musatov Russ. J. Org. Chem. 46 2010 1388 1398
17. B.K. Ghotekar, M.N. Jachak, and R.B. Toche J. Heterocycl. Chem. 46 2009 708 713
18. R. Augusti, and C. Kascheres J. Org. Chem. 58 1993 7079 7083
19. N.P. Peet, and E.W. Huber Heterocycles 35 1993 315 323
20. E.E. Schweizer, and K.J. Lee J. Org. Chem. 49 1984 1964 1969
21. E.E. Schweizer, J.E. Hayes, A. Rheingold, and W. Xu J. Org. Chem. 52 1987 1810 1816
22. F.W. Lichtenthaler, and A. Moser Tetrahedron Lett. 22 1981 4397 4400
23. X. Yang, Y. Jin, H. Liu, Y. Jiang, and H. Fu RSC Adv. 2 2012 11061 11066
24. A. Al-Etaibi, E. John, M.R. Ibrahim, N.A. Al-Awadi, and Y.A. Ibrahim Tetrahedron 67 2011 6259 6274
25. J.C. Sircar, T. Capiris, and S.J. Kesten J. Heterocycl. Chem. 18 1981 117 121
26. Y.A. Ibrahim, N.A. Al-Awadi, and E. John Tetrahedron 64 2008 10365 10374
27. E.E. Schweizer, and J.E. Hayes J. Org. Chem. 53 1988 5562 5564
28. A.A. El-Khamry, S.A. Shiba, A.A. Shalaby, and A.A. Abd Alaha J. Heterocycl. Chem. 43 2006 1189 1193
29. M.A.-M. Sofan, F.M. Abdel-Aziz El-Taweel, T.A. El-Maati, and A.-G. Ali El-Agamey Indian J. Chem., Sect. B 33 1994 738 741
30. S.L. Wang, K. Yang, C.S. Yao, and X.S. Wang Synth. Commun. 42 2012 341 349