Beilstein J. Org. Chem.2014,10, 692–700, doi:10.3762/bjoc.10.62
azomethine ylides, generated in situ from the parent furo[3,2-h]quinoliniums/phenanthroliums, in presence of a copper(II) chloride–phenanthroline catalytic system. The methodology combines general applicability with high yields.
Keywords: copper(II) chloride–phenanthroline; 1,3-dipolar cycloaddition; furo
maleimide derivatives. Our preference for this dienophile was dictated by a recent patent on the lifespan altering properties of cycloadducts involving maleimide dienophiles [20]. Moreover, very recently we have characterized some furo[3,2-h]quinoliniums as potent non-detergent spermicides [19], which
/antifungal/spermicidal/lifespan altering agents, where furo[3,2-h]quinoliniums were employed as dipole precursors and maleimide derivatives as dipolarophiles.
We initially employed the protocols from our recently developed green methodologies [21][22][23][24][25], which however failed to give any promising
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Graphical Abstract
Scheme 1:
Preparation of maleimide dipolarophiles 4a–c.