Fayol, AudeZhu, Jieping2010-11-252010-11-252010-11-25200510.1016/j.tet.2005.09.017https://infoscience.epfl.ch/handle/20.500.14299/58468Three-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)]Aldehydes; Amines Role: RCT (Reactant)RACT (Reactant or reagent) (homoallyl; prepn. of 38a-epoxy-17-naphthyridine derivs. via multicomponent reaction using alpha -isocyano amidehomoallyl amine and aldehyde as reactants); Fragmentation reaction; Stereoselective synthesis (prepn. of 17-naphthyridine derivs. via multicomponent reaction of alpha -isocyano amidehomoallyl amine and aldehydeformation and fragmentation of amino-38a-epoxy-17-naphthyridine intermediates)multicomponent reaction isonitrile isocyano acetonitrile heterocycle naphthyridine diversity; high throughput synthesis multicomponent isonitrile isocyano acetonitrile epoxy naphthyridine; epoxy naphthyridine prepn multicomponent reaction fragmentationtext::journal::journal article::research article