Development of the one-carbon homologation of a 4-methylcoumarin assisted by in-line FTIR

Organic Process Research and Development

Volumn 9, Issue 3, 2005, Pages 356-359

  Horváth, András ^a   De Smet, Koen ^a   Ormerod, Dominic ^a   Depré, Dominique ^a   Pérez Balado, Carlos ^a   Govaerts, Tom ^a   Van Den Heuvel, Dirk ^a   Schorpion, Inge ^a  

^a JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHYLCOUMARIN; COUMARIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; INFRARED SPECTROSCOPY; KINETICS; QUALITATIVE ANALYSIS; SOLVATION;

EID: 20444447576     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op049787u     Document Type: Article

References (8)

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2. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons Inc.: New York, 1999.
3. 2, and N-formyl piperidine.
4. POM-Cl has been used for C-C bond formation in the α-position of (a) esters: Boeckman, R. K., Jr.; Ramaiah, M.; Medwid, J. B. Tetrahedron Lett. 1977, 18(51), 4485;
5. see also Lau, H.-H.; Schoellkopf, U. Liebigs Ann. Chem. 1981, 8, 1378.
6. (b) lactams: Galeazzi, R.; Martelli, G.; Mobbili, G.; Orena, M.; Panagiotaki, M. Heterocycles 2003, 60 (11), 2485
7. Rein, A. R.; Donahue, S. M.; Pavlosky, M. A. Curr. Opin. Drug Discovery Dev. 2000, 3 (6), 734.
8. In a related deprotonation reaction, best results were obtained using a slight excess of starting material over the base, see: Watson, D. J.; Dowdy, E. D.; DePue, J. S.; Kotnis, A. S.; Leung, S.; O'Reilly, B. C. Org. Process Res. Dev. 2004, 8, 616.