ETHYL ALPHA-AMINO-BETA,BETA-DIETHOXYPROPIONATE, A USEFUL SYNTHON FOR THE PREPARATION OF 3,4-FUSED PYRIDINE-6-CARBOXYLATES FROM AROMATIC-ALDEHYDES

Authors
SINGH SK DEKHANE M LEHYARIC M POTIER P DODD RH
Citation
Sk. Singh et al., ETHYL ALPHA-AMINO-BETA,BETA-DIETHOXYPROPIONATE, A USEFUL SYNTHON FOR THE PREPARATION OF 3,4-FUSED PYRIDINE-6-CARBOXYLATES FROM AROMATIC-ALDEHYDES, Heterocycles, 44, 1997, pp. 379-391
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
44
Year of publication
1997
Pages
379 - 391
Database
ISI
SICI code
0385-5414(1997)44:<379:EAAUSF>2.0.ZU;2-O
Abstract
An efficient synthesis of ethyl alpha-amino-beta,beta-diethoxypropiona te (1), via a titanium tetrachloride-catalyzed coupling reaction of et hyl nitroacetate and triethyl orthoformate, is described. Condensation of 1 with various aldehydes followed by reduction and titanium tetrac hloride-promoted cyclization of the products afforded 3,4-fused pyridi ne-6-carboxylates belonging to the azaindole, gamma-carboline and isoq uinoline families of heterocycles.