Synthesis of Alicyclic 2-Methylenethiazolo[2,3-b]quinazolinone Derivatives via Base-Promoted Cascade Reactions

Abstract The synthesis of alicyclic 2-methylenethiazolo[2,3- b ]quinazo­l­inones is performed via base-promoted cascade reactions, starting from either alicyclic β-amino propargylamides using carbon disulfide, or from alicyclic ethyl 2-isothiocyanatocarboxylates by addition of propargylamine. In both cases the cascade reaction proceeds by way of a favoured 5 - exo -dig process during the second ring closure, as confirmed by full NMR spectroscopic assignments. Moreover, a high-yielding retro­-Diels–Alder (RDA) reaction is performed on the norbornene derivatives leading to 2-methylene-2 H -thiazolo[3,2- a ]pyrimidin-5(3 H )-ones. The obtained compounds exert modest antiproliferative activities against a panel of human gynaecological cancer cell lines.