Selective palladium-catalysed carbonylations of dichloroquinoline and simple dichloropyridines

Tetrahedron Letters

Volumn 40, Issue 19, 1999, Pages 3719-3722

  Najiba, Douja ^a   Carpentier, Jean François ^a   Castanet, Yves ^a   Biot, Christophe ^a   Brocard, Jacques ^a   Mortreux, André ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; DICHLOROPYRIDINE DERIVATIVE; DICHLOROQUINOLINE; PALLADIUM; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; MALARIA; MOLECULAR INTERACTION; OXIDATION;

EID: 0033531994     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00597-3     Document Type: Article

References (17)

1. 1. (a) Biot, C.; Glorian, G.; Maciejewski, L. A.; Brocard, J. S.; Domarle, O.; Blampain, G.; Millet, P.; Georges, A. J.; Abessolo, H.; Dive, D.; Lebibi, J. J. Med. Chem. 1997, 40, 3715.
2. (b) Brocard, J.; Lebibi, J.; Maciejewski, L. WO PCT 00721, 1996.
3. 2. (a) Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. "Carbonylation: Direct Synthesis of Carbonyl Compounds" Plenum, New York, 1991.
4. (b) Beller, M. in "Applied Homogeneous Catalysis with Organometallic Compounds" Cornils, B.; Herrmann, W. A. Eds, VCH, Weinheim, 1996, p148.
5. 3. (a) Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem, 1974, 39, 3318.
6. (b) Schoenberg, A.; Bartoletti, I. J. Org. Chem. 1974, 39, 3327.
7. 4. (a) Takeuchi, R.; Suzuki, K.; Sato, N. Synthesis 1990, 923.
8. (b) ibid J. Mol. Catal. 1991, 66, 277.
9. (c) Murata, N.; Sugihara, T., Kondo, Y., Sakamoto, T. Synlett 1997, 298.
10. (d) For palladium-mediated substitution reactions of chlorine in 2-chloroquinolines, see: Ciufolini, M. A.; Mitchell, J. W.; Roschangar, F. Tetrahedron Lett. 1996, 37, 8281.
11. 5. Mono and dialkoxycarbonylation of 2,3-dichloro-5-(methoxymethyl)pyridine: Bessard, Y.; Roduit, J.-P. Tetrahedron 1999, 55, 393.
12. 6. Dialkoxycarbonylation of 2,7-dichloro-1,8-naphtyridin to 2,7-di-(n-butoxycarbonyl)-1,8-naphtyridin was also reported recently: El-ghayoury, A.; Ziessel, R. Tetrahedron Lett. 1998, 39, 4473.
13. 7. Use of HCOONa as the hydrogen source (DMF, 10 atm CO, 140 °C, 10 h) was also inefficient.
14. 8. Hydrocarbonylation is usually performed with aryl iodides or bromides. To the best of our knowledge, no efficient synthesis of aldehyde via aryl chloride hydrocarbonylation has been reported.
15. 2 oxidation of chlorolepidines: Bender, D. R.; Coffen, D. L. J. Het. Chem. 1971, 8, 937.
16. 4: C, 63.67; H, 4.52; N, 5.71; found: C, 63.92; H, 4.28; N, 5.60. IR (KBr): ν 1735 (vs), 1728 (vs).
17. 11. 3-chloropyridine may form either through direct, selective hydrogenolysis of 2,3-dichloropyridine, or more likely via decarbonylation of ester C4a; see ref 5.