New approaches to 6-oxoisoaporphine and tetrahydroisoquinoline derivatives

Helvetica Chimica Acta

Volumn 93, Issue 7, 2010, Pages 1385-1394

  Sobarzo Sánchez, Eduardo ^a   Uriarte, Eugenio ^a   Santana, Lourdes ^a   Tapia, Ricardo A ^b   Lourido, Paulo Pérez ^c  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

^c UNIVERSITY OF VIGO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL BENZOATE; CATALYTIC HYDROGENATION; ISOQUINOLINES; METHOXY; NEW APPROACHES; STARTING MATERIALS; TETRAHYDROISOQUINOLINES;

HYDROGENATION;

1,2,3,4 TETRAHYDRO 6,7 DIMETHOXY 1 (2 METHYLPHENYL)ISOQUINOLINE; 2 (6,7 DIMETHOXY 3,4 DIHYDROISOQUINOLIN 1 YL)BENZYL BENZOATE; 2,3 DIHYDRO 6 HYDROXY 5 METHOXY 7H DIBENZO[DE,H]QUINOLIN 7 ONE; 2,3 DIMETHOXY 5,6,8,12B TETRAHYDROISOINDOLO[1,2 A]ISOQUINOLINE; 6 HYDROXY 5 METHOXY 7H DIBENZO[DE,H]QUINOLIN 7 ONE; 6 OXOISOAPORPHINE; APORPHINE DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 77954911252     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.200900394     Document Type: Article

References (34)

1. Y. Sugimoto, H. A. A. Babiker, S. Inanaga, M. Kato, A. Isogay, Phytochemistry 1999, 52, 1431.
2. B.-W. Yu, L.-H. Meng, J.-Y. Chen, T.-X. Zhou, K.-F. Cheng, J. Ding,G.-W. Qin, J. Nat. Prod. 2001, 64, 968.
3. S. Hu, S. Xu, X. Yao, C. Cui, Y. Tezuka, T. Kikuchi, Chem. Pharm. Bull. 1993, 41, 1866.
4. C. Hou, H. Xue, Acta Pharm. Sin. 1985, 20, 112.
5. S. Iwashima, T. Ueda, H. Honda, T. Tsujioka, M. Ohno, J. Aoki, T. Kan, J. Chem. Soc., Perkin Trans. 1 1984, 2177.
6. G. Pieri, F. M. Carlini, C. Paffoni, G. Boffa, U.S. Patent 4,031,096, 1977;
7. G. Boffa, A. Crotti, G. Pieri, A. Mangini, A. Tundo,U.S. Patent 3,678,053, 1972;
8. G. Ribaldone,G. Borsotti, F. Gonzati,U.S. Patent 3,960,866, 1976;
9. G. Ribaldone, U.S. Patent 3,943,136, 1976;
10. J. King, G. R. Ramage, J. Chem. Soc. 1954, 936;
11. A. K.Wick, Helv. Chim. Acta 1966, 49, 1748;
12. A. K.Wick, Helv. Chim. Acta 1966, 49, 1755.
13. J.-L. Fabre, D. Farge, C. James, U.S. Patent 4,128,650, 1978.
14. G. N. Walker, R. J. Kempton, J. Org. Chem. 1971, 36, 1413.
15. E. Sobarzo-Sánchez, B. K. Cassels, L. Castedo, Synlett 2003, 1647.
16. J. R. De la Fuente, C. Jullian, C. Saitz, V. Neira, O. Poblete, E. Sobarzo-Sánchez, J. Org. Chem. 2005, 70, 8712.
17. E. Sobarzo-Sánchez, J. De la Fuente, L. Castedo, Magn. Reson. Chem. 2005, 43, 1080.
18. J. Kunitomo, S. Kaede, M. Satoh, Chem. Pharm. Bull. 1985, 33, 2778.
19. X. Wang, R. B. Silverman, J. Org. Chem. 1998, 63, 7357;
20. G. A. Olah, B. G. Balaram Gupta, R. Malhotra, S. C. Narang, J. Org. Chem. 1980, 45, 1638;
21. Y. D. Vankar, C. Trinadha Rao, Tetrahedron Lett. 1985, 26, 2717;
22. A. K. Mandal, S. W. Mahajan, Tetrahedron Lett. 1985, 26, 3863;
23. G. Dai-Ho, P. S. Mariano, J. Org. Chem. 1987, 52, 704;
24. I. Fernández, B. García, S. Muñoz, J. R. Pedro, R. de la Salud, Synlett 1993, 7, 489;
25. M. Di Deo, E. Marcantoni, E. Torregiani, G. Bartoli, M. C. Bellucci, M. Bosco, L. Sambri, J. Org. Chem. 2000, 65, 2830.
26. A. Kamal, G. Ramesh, N. Laxman, Synth. Commun. 2001, 31, 827.
27. C. A. Merlic, C. C. Aldrich, J. Albaneze-Walker, A. Saghatelian, J. Am. Chem. Soc. 2000, 122, 3224.
28. G. Dai-Ho, P. S. Mariano, J. Org. Chem. 1988, 53, 5113.
29. W. J. Houlihan, R. E. Manning, U.S. Patents 3,686,207, 3,644,370, 3,644,369, 3,642,777, 1972.
30. L. J. Farrugia, ORTEP-3 for Windows - a version of ORTEP-III with Graphical User Interface (GUI), J. Appl. Crystallogr. 1997, 30, 568.
31. E. Sobarzo-Sánchez, L. Castedo, J. R. De la Fuente, Struct. Chem. 2006, 17, 483.
32. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, SIR-97: A new tool for crystal structure determination and refinement. J. Appl. Crystallogr. 1999, 32, 115.
33. G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.
34. L. J. Farrugia, WinGX suite for small-molecule single-crystal crystallography, J. Appl. Crystallogr. 1999, 32, 837.