Highly stereoselective Friedel-Crafts type cyclization. Facile access to enantiopure 1,4-dihydro-4-phenyl isoquinolinones

Tetrahedron

Volumn 59, Issue 40, 2003, Pages 8049-8056

  Philippe, Nicolas ^a   Denivet, François ^a   Vasse, Jean Luc ^a   Sopkova De Olivera Santos, Jana ^b   Levacher, Vincent ^a   Dupas, Georges ^a  

^a IRCOF   (France)

^b UNIVERSITÉ DE CAEN   (France)

Author keywords

Cyclization; Friedel Crafts reaction; Isoquinolinone; Stereoselective

Indexed keywords

ISOQUINOLINE DERIVATIVE; N (1 PHENYLETHYL) 7 METHOXY 4 PHENYL 1,4 DIHYDROISOQUINOLIN 3 ONE; N BENZYL 7 METHOXY 4 PHENYL 1,4 DIHYDROISOQUINOLIN 3 ONE; N METHYL 4 PHENYL 1,4 DIHYDROISOQUINOLIN 3 ONE; N METHYL 8 ACETAMIDO 4 PHENYL 1,4 DIHYDROISOQUINOLIN 3 ONE; N METHYL 8 BROMO 4 PHENYL 1,4 DIHYDROISOQUINOLIN 3 ONE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; FRIEDEL CRAFTS REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0141852248     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01236-5     Document Type: Article

References (18)

1. Kihara M.;Ikeuchi M.;Adachi S.;Nagao Y.;Moritoki H.;Yamaguchi M.;Taira Z. Chem. Pharm. Bull. 1995;43;1543-1546
2. Kihara M.;Kashimoto M.;Kobayashi S.;Ishida Y.;Moritoki H.; Taira Z. J. Med. Chem. 1990;33;2283-2286
3. (a) Kihara M., Ikeuchi M., Adachi S., Nagao Y., Moritoki H., Yamaguchi M., Taira Z. Chem. Pharm. Bull. 43:1995;1543-1546 (b) Kihara M., Kashimoto M., Kobayashi S., Ishida Y., Moritoki H., Taira Z. J. Med. Chem. 33:1990;2283-2286 (c) Riggs R.M., Nichols D.E., Foreman M.M., Truex L.L., Glock D., Kohli J.D. J. Med. Chem. 30:1987;1454-1458.
4. Kunstmann R., Kruse H., Leven M., Paulus E.F., Schacht U., Schmitt K., Witte P.U. J. Med. Chem. 30:1987;798-804.
5. Philippe N., Levacher V., Dupas G., Quéguiner G., Bourguignon J. Org. Lett. 2:2000;2185-2187.
6. Prat L., Mojovic L., Levacher V., Dupas G., Quéguiner G., Bourguignon J. Tetrahedron: Asymmetry. 9:1998;2509-2516.
7. Nakajima T., Suga S., Sugita T., Ichikawa K. Tetrahedron. 1969;1807-1816.
8. Piccolo O., Azzena U., Melloni G., Delogu G., Valoti E. J. Org. Chem. 56:1991;183-187.
9. Branchaud B.P., Blanchette H.S. Tetrahedron Lett. 43:2002;351-353.
10. Kihara M., Ikeuchi M., Adachi S., Nagao Y., Moritoki H., Yamaguchi M., Taira Z. Chem. Pharm. Bull. 43:1995;1543-1546.
11. Coote J., Davies S.G., Middlemiss D., Naylor A. Tetrahedron: Asymmetry. 1:1990;33-56.
12. Recrystallization of the crude product from isopropanol afforded 5a in 40% yield and 97% ee (S).
13. During the preparation of benzazepines, O-demethylation is also observed in the course of similar electrophilic cyclization Gerritz S.W., Smith J.S., Nanthakumar S.S., Uehling D.E., Cobb J.E. Org. Lett. 25:2000;4099-4102.
14. Crystallographic data for (S,S)-5e available from the Cambridge structural database (CSD).
15. Zàra-Kacziàn E.;György L.;Deàk G.;Seregi A.;Dodà M. J. Med. Chem. 1986;29;1189-1195
16. (a) Zàra-Kacziàn E., György L., Deàk G., Seregi A., Dodà M. J. Med. Chem. 29:1986;1189-1195 (b) Aboul-Enein H.Y., Islam M.R., Bakr S.A. J. Liq. Chromatogr. 11:1988;1485-1493.
17. Dandridge P.A.;Kaiser C.;Brenner M.;Gaitonopoulos D.;Sarau H.M. J. Med. Chem. 1984;27;28-35
18. (a) Dandridge P.A., Kaiser C., Brenner M., Gaitonopoulos D., Sarau H.M. J. Med. Chem. 27:1984;28-35 (b) Venkov A.P., Vodenicharov D.M. Synthesis. 1990;253-255.