MODELS OF FOLATE COENZYMES 13. SYNTHESES OF BENZOQUINOLIZINE AND INDOLOQUINOLIZINE DERIVATIVES VIA CARBON FRAGMENT TRANSFER FROM FLOATE COENZYME MODELS

Article abstract of DOI:10.1016/S0040-4020(01)96686-4

Anions of β,β-disubstituted acetyl acetates (2, CH2COCR₁R₂COOR₃; R₁=R₂=Me2, R₁=Et, R₂=COOMe, R₁=Et, R₂=SPh) add to 1-tosyl-3,4,4-trimethyl-Δ-imidazolinium iodide (3) to give the corresponding imidazolines (4), which are regarded as models of methylenetetrahydrofolate.These models transfer C(2) of the imidazalodine -with its appended carbon fragment- to tryptamine and 2-(3,4-dimethoxybenzene)ethyl amine to yield enaminoketo ester intermediates which can be converted into benzoquinolizine and indolo<2,3-a>quinolizine derivatives, respectively, in two cyclization steps.The intermediate derived from transfer of carbon fragment =CH-CH2COC(SPh)(Et)COOMe to tryptamine exhibits reactions which involve nucleophilic displacement at a sulphur atom of a thio ether bond.