New synthetic approaches to CNS drugs. A straightforward, efficient synthesis of tetrahydroindol-4-ones and tetrahydroquinolin-5-ones via palladium-catalyzed oxidation of hydroxyenaminones

Tetrahedron Letters

Volumn 43, Issue 44, 2002, Pages 7929-7932

  Pita, Beatriz ^a   Masaguer, Christian F ^a   Raviña, Enrique ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Cyclic ketones; Enamines; Tetrahydroindoles; Tetrahydroquinolines

Indexed keywords

BUTYROPHENONE DERIVATIVE; CHEMICAL COMPOUND; HYDROXYENAMINONE; INDOLE; NEUROLEPTIC AGENT; PALLADIUM; QUINOLINE; TETRAHYDROINDOL 4 ONE; TETRAHYDROQUINOLIN 5 ONE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; CYCLIZATION; OXIDATION;

EID: 0037190872     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01901-9     Document Type: Article

References (13)

1. Brea J., Rodrigo J., Carrieri A., Sanz F., Cadavid M.I., Enguix M.J., Villazón M., Mengod G., Caro Y., Masaguer C.F., Raviña E., Centeno N.B., Carotti A., Loza M.I. J. Med. Chem. 45:2002;54-71.
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4. Bilbao E.R., Alvarado M., Masaguer C.F., Raviña E. Tetrahedron Lett. 43:2002;3551-3554.
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9. General Procedure: A mixture of the γ-hydroxyenaminone 3a-d (1 mmol), mesityl bromide (1.1 mmol), palladium acetate (0.03 mmol), triphenylphosphine (0.06 mmol), potassium carbonate (1.2 mmol) and DMF (5 ml) was heated at 150°C for 4 h. The resulting mixture was filtered through a Celite pad and then evaporated under reduced pressure to give an oily residue, which was purified by column chromatography to give the corresponding quinolines.
10. 3-Ph).
11. General Procedure: To a solution of the β-hydroxyenaminone 3e-g (1 mmol) in 5 ml of DMF, mesityl bromide (1 mmol), tetrakis(triphenylphosphine)palladium(0) (0.025 mmol), and potassium carbonate (2 mmol) was added, and the mixture heated at 150°C for 2 h. After cooling, the mixture was filtered through a Celite pad and evaporated in vacuo to give an oily residue, which was purified by column chromatography to yield the corresponding indoles.
12. 3).
13. 13C NMR, FTIR, MS). Yields given correspond to isolated pure compounds.