Multicomponent synthesis of epoxy-tetrahydronaphthyridine and structural diversification by subsequent fragmentation

Three-component reaction of an alpha -(isocyano)acetamide, a homoallyl amine and an aldehyde in methanol at room temp. provides an oxa-bridged tricyclic compd. in good to excellent yield as a mixt. of two separable diastereoisomers. In this one-pot multicomponent process, one C-N, one C-O and three C-C bonds are formed with concomitant creation of five asym. centers and three rings. Fragmentation of (epoxy)tetrahydro naphthyridine affords differentially substituted 5,6,7,8-tetrahydro-1,7-naphthyridine derivs., depending on the reaction conditions, providing thus addnl. structural diversity. A one-pot three-component synthesis of 5,6,7,8-tetrahydro-1,7-naphthyridine derivs. is also documented. [on SciFinder (R)]


Published in:
Tetrahedron, 61, 48, 11511-11519
Year:
2005
Keywords:
Note:
CAN 144:88193
28-2
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.
Journal
0040-4020
written in English.
872211-08-0P; 872216-31-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of 1,7-naphthyridine derivs. via multicomponent reaction of alpha -(isocyano)acetamide, homoallyl amine and aldehyde, formation and fragmentation of amino-3,8a-epoxy-1,7-naphthyridine intermediates); 872211-17-1P; 872211-18-2P; 872211-19-3P; 872211-20-6P; 872211-21-7P; 872211-22-8P; 872211-23-9P; 872211-24-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of 1,7-naphthyridine derivs. via multicomponent reaction of alpha -isocyano amide, homoallyl amine and aldehyde, formation and fragmentation of amino-3,8a-epoxy-1,7-naphthyridine intermediates); 78-84-2; 104-53-0 (3-Phenylpropanal); 111-71-7 (Heptanal); 1440-29-5; 120301-86-2; 120301-87-3; 123613-53-6; 872211-03-5; 872211-04-6; 872211-06-8; 872211-07-9 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of 3,8a-epoxy-1,7-naphthyridine derivs. via multicomponent reaction using alpha -isocyano amide, homoallyl amine and aldehyde as reactants); 85059-38-7P; 85059-48-9P; 85059-51-4P; 336105-88-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of 3,8a-epoxy-1,7-naphthyridine derivs. via multicomponent reaction using alpha -isocyano amide, homoallyl amine and aldehyde as reactants); 872211-16-0P Role: BYP (Byproduct), PREP (Preparation) (prepn. of amino-3,8a-epoxy-1,7-naphthyridine derivs. via multicomponent reaction using alpha -isocyano amide, homoallyl amine and aldehyde as reactants); 872211-09-1P; 872211-10-4P; 872211-11-5P; 872211-12-6P; 872211-13-7P; 872211-14-8P; 872211-15-9P; 872216-32-5P; 872216-33-6P; 872216-34-7P; 872216-35-8P; 872216-36-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of amino-3,8a-epoxy-1,7-naphthyridine derivs. via multicomponent reaction using alpha -isocyano amide, homoallyl amine and aldehyde as reactants)
Laboratories:




 Record created 2010-11-25, last modified 2018-12-03


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