Synthesis of optically active α-aminobenzolactam via an oxidative-cyclization reaction

Tetrahedron Asymmetry

Volumn 14, Issue 14, 2003, Pages 2081-2085

  Chang, Ching Yao ^a   Yang, Teng Kuei ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

1 (METHOXY 2 OXO 2,3,4,5 TETRAHYDRO 1H BENZ[B]AZEPIN 3 YL)CARBAMIC ACID BENZYL ESTER; 1 (METHOXYCARBAMOYL 3 PHENYLPROPYL)CARBAMIC ACID BENZYL ESTER; 3 AMINO 1,3,4,5 TETRAHYDROBENZ[B]AZEPIN 2 ONE ALPHA AMINOBENZOLACTAM; BENZYL DERIVATIVE; LACTAM DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; OPTICS; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0037969118     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00408-7     Document Type: Article

References (17)

1. Watthey J.W.H., Stanton J.L., Desai M., Babiarz J.E., Finn B.M. J. Med. Chem. 28:1985;1511.
2. Boyer S.K., Pfund R.A., Portmann R.E., Sedelmeier G.H., Wetter H.F. Helv. Chim. Acta. 71:1988;337.
3. Tamura S.Y., Goldman E.A., Bergum P.W., Semple J.E. Bioorg. Med. Chem. Lett. 9:1999;2573.
4. Ho J.Z., Gibson T.S., Semple J.E. Bioorg. Med. Chem. Lett. 12:2002;743.
5. Smith R.G., Cheng K., Schoen W.R., Pong S.S., Hickey G., Jacks T., Butler B., Chan W.W.S., Chaung L.Y.P., Judith F., Taylor J., Wyvratt M.J., Fisher M.H. Science. 260:1993;1640.
6. Schoen W.R., Pisano J.M., Prendergast K., Wyvratt M.J. Jr., Fischer M.H., Cheng K., Wanda W.S., Butler B., Smith R.G., Ball R.G. J. Med. Chem. 37:1994;897.
7. Armstrong J.D. III, Eng K.K., Keller J.L., Purick R.M., Hartner F.W. Jr., Choi W.B., Askin D., Volante R.P. Tetrahedron Lett. 35:1994;3239.
8. Jackson R.F.W., Moore R.J., Dexter C.S. J. Org. Chem. 63:1998;7875.
9. Gleave D.M., Brickner S.J. J. Org. Chem. 61:1996;6470.
10. Fleming I., Moses R.C., Tercel M., Ziv J. J. Chem. Soc., Perkin Trans. 1. 1991;617.
11. Ritter A.R., Miller M.J. J. Org. Chem. 59:1994;4602.
12. Kikugawa Y., Kawase M. Chem. Lett. 1990;581.
13. Romero A.G., Darlington W.H., Jacobsen E.J., Mickelson J.W. Tetrahedron Lett. 37:1996;2361.
14. Wardrop D.J., Basak A. Org. Lett. 3:2001;1053.
15. Romero A.G., Darlington W.H., McMillan M.W. J. Org. Chem. 62:1997;6582.
16. + 359.1608.
17. 4 (pH 2) and detected by a UV lamp at λ=254 nm. The retention times of the R- and S-forms were 9.4 min and 11.6 min, respectively.