A novel three-component synthesis of tetrahydrofuro[2,3-c]pyridines I (R1 = PhCH2; R2 = EtO2C; R3 = Me2CH, n-hexyl, PhCH2CH2, 4-O2NC6H4, etc.; R4R5N = morpholino, piperidino, pyrrolidino, diethylamino) from readily accessible starting materials is described. Simply heating a toluene soln. of an aminopentynoate R1NH(CH2)2C==CR2, an aldehyde R3CHO, and an alpha -isocyanoacetamide R4CH(NC)CONR5R6 (R4 = H, PhCH2) in the presence of ammonium chloride provided I in good to excellent yields. The fused ring system is produced in this one-pot process by the concomitant formation of five chem. bonds. [on SciFinder (R)]
Title
Synthesis of Polysubstituted 4,5,6,7-Tetrahydrofuro[2,3-c]pyridines by a Novel Multicomponent Reaction
Published in
Organic Letters
Volume
6
Issue
1
Pages
115-118
Date
2004
ISSN
1523-7060
Note
CAN 140:128304
28-2
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
78-84-2 (Isobutanal); 100-52-7 (Benzaldehyde); 104-53-0 (3-Phenylpropanal); 111-71-7 (Heptanal); 123-11-5 (4-Methoxybenzaldehyde); 555-16-8 (4-Nitrobenzaldehyde); 18545-16-9 (5-Acetoxypentanal); 67434-29-1; 85059-38-7; 85059-48-9; 85059-51-4; 107301-61-1; 142301-77-7; 500555-97-5 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of polysubstituted tetrahydrofuropyridines via three-component condensation of amino pentynoate, aldehydes, and alpha -isocyano acetamides); 651021-97-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of polysubstituted tetrahydrofuropyridines via three-component condensation of amino pentynoate, aldehydes, and alpha -isocyano acetamides); 651021-98-6P; 651021-99-7P; 651022-00-3P; 651022-01-4P; 651022-02-5P; 651022-03-6P; 651022-04-7P; 651022-05-8P; 651022-06-9P; 651022-07-0P; 651022-08-1P; 651022-09-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of polysubstituted tetrahydrofuropyridines via three-component condensation of amino pentynoate, aldehydes, and alpha -isocyano acetamides)
Record creation date
2010-11-25
