Regioselective synthesis of 2-methyl-2,5,6,11,12,13-hexahydro 4H indazolo[5,4-a]pyrrolo[3,4-c]carbazole-4-ones

Journal of Heterocyclic Chemistry

Volumn 46, Issue 6, 2009, Pages 1185-1189

  Tao, Ming ^a   Park, Chung Ho ^a   Josef, Kurt ^a   Hudkins, Robert L ^a  

^a CEPHALON INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYL 11 (1 METHYLETHYL) 8 (PYRIMIDIN 2 YLOXY) 2,5,6,11,12,13 HEXAHYDRO 4H INDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOL 4 ONE; 2 METHYL 11 BUTYL 8 (PYRIMIDIN 2 YLOXY) 2,5,6,11,12,13 HEXAHYDRO 4H INDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOL 4 ONE; 2 METHYL 11 CYCLOPENTYL 8 (PYRIMIDIN 2 YLOXY) 2,5,6,11,12,13 HEXAHYDRO 4H INDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOL 4 ONE; 2 METHYL 11 CYCLOPROPYLMETHYL 8 (PYRIMIDIN 2 YLOXY) 2,5,6,11,12,13 HEXAHYDRO 4H INDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOL 4 ONE; 2 METHYL 2,5,6,11,12,13 DIHYDROINDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOLE 6 ONE; 2 METHYL 2,5,6,11,12,13 HEXAHYDRO 4H INDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOLE 4 ONE DERIVATIVE; 2 METHYL 2,5,6,11,12,13 HEXAHYDROINDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOLE 4 ONE; 2 METHYL 5 [5 TRIS(1 METHYLETHYL)SILYLOXY 1H INDOL 2 YL] 4,5,6,7 TETRAHYDRO 2H INDAZOL 5 OL; 2 METHYL 8 (PYRIMIDIN 2 YLOXY) 11 ETHYL 2,5,6,11,12,13 HEXAHYDRO 4H INDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOL 4 ONE; 2 METHYL 8 (PYRIMIDIN 2 YLOXY) 2,5,6,11,12,13 HEXAHYDRO 4H INDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOL 4 ONE; 2 METHYL 8 HYDROXY 2,5,6,11,12,13 HEXAHYDO 4H INDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOL 4 ONE; 2,11 DIMETHYL 8 (PYRIMIDIN 2 YLOXY) 2,5,6,11,12,13 HEXAHYDRO 4H INDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOL 4 ONE; 4 CYANO 5 ETHOXYCARBONYL 2,10,11,12 TETRAHYDRO 2 METHYLINDAZOLO[5,4 A]CARBAZOLE; 5 (1H INDOL 2 YL) 2 METHYL 6,7 DIHYDRO 1H INDAZO 5 OL; 5 (1H INDOL 2 YL) 2 METHYL 6,7 DIHYDRO 2H INDAZOLE; 5 [[TRIS(1 METHYLETHYL)SILYL]OXY] 1H INDOLE; 5 CYANO 2 METHYL 4 ETHOXYCARBONYL 7 HYDROXY 2,10,11,12 TETRAHYDRO 4H INDAZOL[5,4 A]CARBAZOLE; 5 CYANO 4 ETHOXYCARBONYL 2,10,11,12 TETRAHYDRO 2 METHYL [7 TRIS(1 METHYLETHYL)SILYLOXY]INDAZOLO[5,4 A]CARBAZOLE; 5 CYANO 4 ETHOXYCARBONYL 2,10,11,12 TETRAHYDRO 2 METHYL[7 TRIS(1 METHYLETHYL)SILYLOXY]INDAZOLO[5,4 A]CARBAZOLE; 5 CYANO 4 ETHOXYCARBONYL 2,10,11,12 TETRAHYDRO 2 METHYLINDAZOLO[5,4 A]CARBAZOLE; 8 PYRIMIDINYLOXY 2,5,6,11,12,13 HEXAHYDRO 4H INDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOLE 4 ONE; CARBAZOLE DERIVATIVE; CEP 1347; DUAL LEUCINE ZIPPER BEARING KINASE; HEXAHYDROINDAZOLO[5,4 A]PYRROLO[3,4 C]CARBAZOLE 4 ONE; INDAZOLE DERIVATIVE; LEUCINE ZIPPER PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 72249108384     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.200     Document Type: Article

References (15)

1. (a) Murakata, C.; Kaneko, M.; Gessner, G.; Angeles, T. S.; Ator, M. A.; O'kane, T. M.; McKenna, B. A. W.; Thomas, B. A.; Mathiasen, J. R.; Saporito, M. S.; Bozyczko-Coyne, D.; Hudkins, R. L. Bioorg Med Chem Lett 2002, 12, 147;
2. (b) Bozyczko-Coyne, D.; Saporito, M. S.; Hudkins, R. L. Curr Drug Targets CNS Neurol Disord 2002, 1, 31;
3. (c) Saporito, M. A.; Hudkins, R. L.; Maroney, A. C. Prog Med Chem 2002, 40, 23.
4. (a) Hudkins, R. L.; Johnson, N. W.; Angeles, T. S.; Gessner, G. W.; Mallamo, J. P. J Med Chem 2007, 50, 433;
5. (b) Hudkins, R. L.; Diebold, J. L.; Tao, M.; Josef, K. L.; Park, C. H.; Angeles, T. S.; Aimone, L. D.; Husten, J.; Ator, M. A.; Meyer, S. L.; Holskin, B. P.; Durkin, J. T.; Fedorov, A. A.; Fedorov, E. V.; Almo, S. C.; Mathiason, J. R.; Bozyczko-Coyne, D.; Saporito, M. S.; Scott, R. W.; Mallamo, J. P. J Med Chem 2008, 51, 5680.
6. (a) Hudkins, R. L.; Park, C.-H. J Heterocycl Chem 2003, 40, 135;
7. (b) Hudkins, R. L.; Reddy, D. R.; Tao, M.; Underiner, T. L.; Zulli, A. L. U.S. Pat.2,005,137,245 (2005).
8. (a) Broka, C. A. Eur. Pat.695,755 (1996);
9. (b) Jones, R. A.; Fresneda, P. M. Tetrahedron 1999, 40, 4837;
10. (c) Ziegler, F. E.; Spitzner, E. B.; Wilkins, C. K. J Org Chem 1971, 36, 1759;
11. (d) Pindur, U.; Kim, M.-H. Heterocycles 1988, 27, 967.
12. (a) Josef, K. A.; Dandu, R.; Tao, M.; Hudkins, R. L. J Heterocycl Chem 2006, 43, 719;
13. (b) Reddy, D. R.; Tao, M.; Josef, K. A.; Bacon, E. R.; Hudkins, R. L. J Heterocycl Chem 2007, 44, 437.
14. Katritzky, A.; Akutagava, K. Tetrahedron Lett 1985, 26, 5935.
15. Maroney, A. C.; Finn, J. P.; Connors, T. J.; Durkin, J. T.; Angeles, T.; Gessner, G.; Xu, Z.; Meyer, S. L.; Savage, M. J.; Greene, L. A.; Scott, R. W.; Vaught, J. L. J Biol Chem 2001, 276, 25302.