88839-24-1Relevant articles and documents
MODELS OF FOLATE COENZYMES 13. SYNTHESES OF BENZOQUINOLIZINE AND INDOLOQUINOLIZINE DERIVATIVES VIA CARBON FRAGMENT TRANSFER FROM FLOATE COENZYME MODELS
Stoit, Axel R.,Pandit, Upendra K.
, p. 3345 - 3354 (1985)
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 indoloquinolizine 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.