Synthesis and stereochemistry of azeto[2,1-a]isoquinolin-2-one derivatives

Arkivoc

Volumn 2003, Issue 5, 2003, Pages 87-93

  Csomós, Péter ^a   Martinek, Tamás A ^a   Lázár, László ^a   Fülöp, Ferenc ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

Author keywords

lactam; Isoquinoline; Stereochemistry

Indexed keywords

7,8 DIETHOXY 1 PHENOXY 9B PHENYL 1,4,5,9B TETRAHYDRO 2H AZETO[2,1 A]ISOQUINOLIN 2 ONE; 7,8 DIETHOXY 1,9B DIPHENYL 1,4,5,9B TETRAHYDRO 2H AZETO[2,1 A]ISOQUINOLIN 2 ONE; 7,8 DIETHOXY 9B PHENYL 1 PHTHALIMIDO 1,4,5,9B TETRAHYDRO 2H AZETO[2,1 A]ISOQUINOLIN 2 ONE; 7,8 DIMETHOXY 1 PHENOXY 9B PHENYL 1,4,5,9B TETRAHYDRO 2H AZETO[2,1 A]ISOQUINOLIN 2 ONE; 7,8 DIMETHOXY 1,9B DIPHENYL 1,4,5,9B TETRAHYDRO 2H AZETO[2,1 A]ISOQUINOLIN 2 ONE; CHLORIDE; ISOQUINOLINE DERIVATIVE; PHENOXYACETIC ACID; PHOSPHORUS OXYCHLORIDE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STAUDINGER REACTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 3142580902     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. Gómez-Gallego, M.; Mancheno, M. J.; Sierre, M. A. Tetrahedron 2000, 56, 5743.
2. Fülöp, F. Chem. Rev. 2001, 101, 2181.
3. Bacchi, S.; Bongini, A.; Pannuzio, M.; Villa, M. Synlett 1998, 843.
4. Fülöp, F.; Bernáth, G.; Pihlaja, K. Adv. Heterocyclic Chem. 1998, 69, 349.
5. Rosenblum, S. B.; Huynh, T.; Alfonso, A.; Davis, H. R.; Yumibe, N.; Clader, J. W.; Burnett, D. A. J. Med. Chem. 1998, 41, 973.
6. Bonneau, P. R.; Hasani, F.; Plouffe, C.; Malenfant, E.; LePlante, S. R.; Guse, I.; Ogilive, W. W.; Plante, R.; Davidson, W. C.; Hopkins, J. L.; Morelock, M. M., Cordingley, M. G.; Déziel, R. J. Am. Chem. Soc. 1999, 121, 2965.
7. Banik, B. K.; Becker, F. F. Tetrahedron Lett. 2000, 41, 6551.
8. Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905.
9. Banik, I.; Becker, F. F.; Banik, B. K. J. Med. Chem. 2003, 46, 12.
10. Banik, I.; Hackfeld, L.; Banik, B. K. Heterocycles 2003, 59, 505.
11. Fülöp, F.; Bernáth, G. Curr. Org. Chem. 1999, 3, 1.
12. Fülöp, F.; Kóbor, J.; Bernáth, G.; Sohár, P. Bio-Organic Heterocycles Elsevier Science Ltd., Amsterdam, 1986, 155.
13. Bernáth, G.; Kóbor, J.; Fülöp, F.; Sohár, P.; Argay, G.; Kálmán, A. Tetrahedron 1986, 42, 5139.
14. Bernáth, G.; Fülöp, F.; Árva, J.; Kóbor, J.; Sohár, P. J. Heterocyclic Chem. 1991, 28, 353.
15. Kóbor, J.; Fülöp, F.; Bernáth, G.; Sohár, P. Tetrahedron 1987, 43, 1887.
16. Bose, A. K.; Amin, S. G.; Kapur, J. C.; Manhas, M. S. J. Chem. Soc., Perkin Trans. 1 1976, 2193.
17. Fodor, L.; Szabó, J.; Sohár, P. Tetrahedron 1981, 37, 963.
18. Sohár, P.; Fodor, L.; Szabó, J.; Bernáth, G. Tetrahedron 1984, 40, 4387.
19. Allman, R.; Debaerdemaeker, T.; Kiehl, Georges; Luttringer, J-P.; Tschamber, T.; Wolff, G.; Streith, J. Liebigs Ann. Chem. 1983, 1361.
20. Sharma, S. D.; Mehra, U.; Kaur, V. Ind. J. Chem. 1987, 26, 776.
21. Lal, B.; Bhedi, D. N.; Gidwani, R. M.; Sankar, C. Tetrahedron 1994, 50, 9167.
22. Hatam, M.; Köpper, S.; Martens, J. Heterocycles 1996, 43, 675.
23. The compounds studied were racemates. In Scheme 1 only one enantiomer is shown..
24. Zhao, B.-X.; Yu, Y.; Eguchi, S. Org. Prep. Proc. Int. 1997, 29, 185.
25. Golding, B. T.; Hall, D. R. J. Chem. Soc., Perkin Trans. 1 1975, 1305.