Oxidation of indolines with Fremy's salt: A mechanistic proposal

Tetrahedron Letters

Volumn 38, Issue 49, 1997, Pages 8483-8486

  Giethlen, Bruno ^a   Schaus, John M ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDROXYINDOLE DERIVATIVE; INDOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ISOMERISM; OXIDATION; REACTION ANALYSIS;

EID: 0030721023     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10306-9     Document Type: Article

References (13)

1. A theoretical study on the interaction of (±)-1 with serotonin receptors has been published: Mazurek, A.P.; Weinstein, H.; Osman, R.; Topiol, S.; Ebersole, B.J. Int. J. Quantum Chem., Quantum Biol. Symp. 1984, 11, 183.
2. Kaiser, C.; Kruse, L.I. Eur. Pat. Appl. 1985, EP 162695. CAN 104:168360.
3. Martinelli, M.J.; Leanna, M.R.; Varie, D.L.; Peterson, B.C.; Kress, T.J.; Wepsiec, J.P.; Khau, V.V. Tetrahedron Letters 1990, 31(52), 7579.
4. Zimmer, H.; Lankin, D.C.; Horgan, S.W. Chem. Rev. 1971, 71(2), 229.
5. a. Teuber, H.-J.; Staiger, G. Chem. Ber. 1954, 87(9), 1251.
6. b. Teuber, H.-J.; Staiger, G. Chem. Ber. 1956, 89(2), 489.
7. c. Stadler, P.A.; Frey, A.J.; Troxler, F.; Hofmann, A. Helv. Chim. Acta 1964, 47(3), 756.
8. d. Humber, L.G.; Ferdinandi, E.; Demerson, C.A.; Ahmed, S.; Shah, U.; Mobilio, D.; Sabatucci, J.; DeLange, B.; Labbadia, F.; Hughes, P.; DeVirgilio, J.; Neuman, G.; Chau, T.T.; Weichman, B.M. J. Med. Chem. 1988, 31(9), 1712.
9. -1. UV-Vis (MeOH): 271 nm (log ε 4.14), shoulder to 400 nm.
10. 3 requires C, 70.19; H, 5.63; N, 8.69.
11. a. Kita, Y.; Tohma, H.; Inagaki, M.; Hatanaka, K. Heterocycles 1992, 33(2), 503.
12. see also: b. Cromartie, R.I.T.; Harley-Mason, J. J. Chem. Soc. 1952, 2525.
13. c. Harley-Mason, J. Chem. and Ind. 1952, 173.