'One-pot' four-step synthesis of cerpegin

Tetrahedron Letters

Volumn 46, Issue 22, 2005, Pages 3811-3813

  Lazaar, Jalal ^a   Hoarau, Christophe ^a   Mongin, Florence ^a   Trécourt, Francois ^a   Godard, Alain ^a   Quéguiner, Guy ^a   Marsais, Francis ^a  

^a UNIVERSITÉ ET INSA DE ROUEN   (France)

Author keywords

Carboxylic acid; Cerpegin; Lithiation; Pyridines

Indexed keywords

1,1 DIMETHYL 3,4 DIOXO 1,3,4,5 TETRAHYDROFURO[3,4 C]PYRIDINE; ACETONE; ACID; ALKALOID DERIVATIVE; CERPEGIN; CESIUM; CESIUM CARBONATE; LITHIUM SALT; METHOXYNICOTINIC ACID; METHYL IODIDE; NICOTINIC ACID DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKYLATION; ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; LITHIATION; LOW TEMPERATURE;

EID: 18144406124     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.176     Document Type: Article

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15. These conditions were successful for 2-chloronicotinic acid; see Ref. 11
16. After the dilithium salts 3 were hydrolyzed by adding water (0.5 mL), THF was removed under reduced pressure. A 2 M aqueous solution of HCl (0.5 mL), AcOH (5 mL) and EtOH (10 mL) were then added to the crude material and the resulting solution was heated at reflux for 3 h
17. 5), 1.62 (s, 6H, 2Me); m/z (EI): 197-199 (70%), 182-184 (100%)
18. 5, J = 5.3 Hz), 1.41 (s, 6H, 2Me); m/z (EI): 241-243 (10%), 226-228 (100%)
19. After the dilithium salts 3 was first hydrolyzed by adding water (0.5 mL), THF was removed under reduced pressure. A 33% acetic solution of HBr (10 mL) was then added to the crude material and the resulting solution was heated at reflux for 3 h
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21. 4