Microwave-assisted, solvent-free synthesis of 1-(α- or β-hydroxynaphthyl)-1,2,3,4-tetrahydroisoquinolines by the Mannich reaction

Tetrahedron Letters

Volumn 47, Issue 23, 2006, Pages 3881-3883

  Szatmári, István ^a   Lázár, László ^a   Fülöp, Ferenc ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

Author keywords

1 Naphthol; 2 Naphthol; Dihydroisoquinoline; Mannich reaction; Nucleophilic addition

Indexed keywords

1 NAPHTHOL; 2 NAPHTHOL; 3 METHYL 6,7 DIMETHOXY 3,4 DIHYDROISOQUINOLINE; ISOQUINOLINE DERIVATIVE; NAPHTHOL DERIVATIVE; SOLVENT; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CIS ISOMER; MANNICH REACTION; MICROWAVE RADIATION; STEREOCHEMISTRY;

EID: 33646132492     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.169     Document Type: Article

References (27)

1. Chrzanowska M., and Rozwadowska M.D. Chem. Rev. 104 (2004) 3341-3370
2. Vicario J.L., Badía D., Carrillo L., and Etxebarria J. Curr. Org. Chem. 7 (2003) 1775-1792
3. Kaufman T.S. Tetrahedron: Asymmetry 15 (2004) 1203-1237
4. Kaufman T.S. Synthesis (2005) 339-360
5. Bentley K.W. Nat. Prod. Rep. 22 (2005) 249-268
6. Pelletier J.C., and Cava M.P. Synthesis (1987) 474-477
7. Chrzanowska M. Tetrahedron: Asymmetry 13 (2002) 2497-2500
8. Taylor A.M., and Schreiber S.L. Org. Lett. 8 (2006) 143-146
9. Szatmári I., and Fülöp F. Curr. Org. Synth. 1 (2004) 155-165
10. Szatmári I., Martinek T.A., Lázár L., and Fülöp F. Tetrahedron 59 (2003) 2877-2884
11. Szatmári I., Martinek T.A., Lázár L., Koch A., Kleinpeter E., Neuvonen K., and Fülöp F. J. Org. Chem. 69 (2004) 3645-3653
12. Cardellicchio C., Ciccarella G., Naso F., Perna F., and Tortorella P. Tetrahedron 55 (1999) 14685-14692
13. Wang X., Dong Y., Sun J., Xu X., Li R., and Hu Y. J. Org. Chem. 70 (2005) 1897-1900
14. Dong Y., Li R., Lu J., Xu X., Wang X., and Hu Y. J. Org. Chem. 70 (2005) 8617-8620
15. Dale W.J., Starr L., and Strobel C.W. J. Org. Chem. 26 (1961) 2225-2227
16. Reimann E., and Grasberger F. Monatsh. Chem. 136 (2005) 193-209
17. 2O-EtOAc (2:1). Yields: 3: 0.16 g (40%); 4: 0.18 g (35%); 5: 0.27 g (65%); 6: 0.28 g (56%); 8: 0.21 g (40%); 9: 0.31 g (60%, 9a:9b = 3:1), 9a and 9b were separated by column chromatography, with EtOAc-n-hexane (3:1) as eluent.
18. 3): 22.6; 36.3; 50.5; 56.8; 56.8; 58.3; 110.5; 112.0; 113.5; 113.7; 115.0; 119.6; 126.7; 128.4; 130.9; 132.5; 134.7; 134.8; 139.0; 140.0; 154.3; 156.4.
19. Kappe C.O. Angew. Chem., Int. Ed. 43 (2004) 6250-6284
20. Kaval N., Halasz-Dajka B., Vo-Thanh G., Dehaen W., Van der Eycken J., Mátyus P., Loupy A., and Van der Eycken E. Tetrahedron 61 (2005) 9052-9057
21. Devi I., and Bhuyan P.J. Tetrahedron Lett. 46 (2005) 5725-5729
22. 2O-EtOAc (2:1). Yields: 3: 0.27 g (65%); 4: 0.28 g (56%); 5: 0.35 g (85%); 6: 0.36 g (72%); 8: 0.32 g (61%); 9: 0.44 g (84%, 9a:9b = 2.6:1), 9a and 9b were separated by column chromatography, with EtOAc-n-hexane (3:1) as eluent.
23. Szatmári I., Martinek T.A., Lázár L., and Fülöp F. Eur. J. Org. Chem. (2004) 2231-2238
24. Fülöp F., Tari J., Bernáth G., and Sohár P. Heterocycles 43 (1996) 1605-1606
25. Cimarelli C., Mazzanti A., Palmieri G., and Volpini E. J. Org. Chem. 66 (2001) 4759-4765
26. Liu D.-X., Zhang L.-C., Wang Q., Da C.-S., Xin Z.-Q., Wang R., Choi M.C.K., and Chan A.S.C. Org. Lett. 3 (2001) 2733-2735
27. Ji J.-X., Qiu L.-Q., Yip C.W., and Chan A.S.C. J. Org. Chem. 68 (2003) 1589-1590