The reaction of isoquinoline or quinoline with dialkyl acetylenedicarboxylates in the presence of alkyl 2-{3,5-dioxo-5H-thiazolo[3,2-a]pyrimidin-2(3H)-ylidene}acetates (generated in situ from acetylenedicarboxylates and 2-thiouracils) led to dialkyl 2-(2-alkoxy-2-oxoethylidene)-5-oxo-2H,5H,11b′H-spiro{thiazolo[3,2-a]pyrimidine-3,2′-[1,3]oxazino[2,3-a]isoquinoline}-3′,4′-dicarboxylates or dialkyl 2-(2-alkoxy-2-oxoethylidene)-5-oxo-2H,4a′H,5H-spiro{thiazolo[3,2-a]pyrimidine-3,2′-[1,3]oxazino[3,2-a]quinoline}-1′,2′-dicarboxylates in good yields. The structure of the target compounds was confirmed by X-ray diffraction study.
Ketenimine N-Functionalization of Thiazolidine-3,4-diones with Acetylenes and Isocyanides. -The three-component one-pot reaction of thiazolidinediones with alkyl isocyanides and dialkyl acetylenedicarboxylates gives highly functionalized stable ketenimines. A plausible mechanism is provided. -(YAVARI*, I.; SANAEISHOAR, T.; AZAD, L.; GHAZVINI, M.; Mendeleev Commun. 21 (2011) 2, 108-109, http://dx.
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