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A one pot multicomponent protocol is described herein as an approach for construction of spirooxazolidine‐2‐thiones and spirooxothiolane‐2‐imines. In a DBU mediated reaction, isatin, phenyl acetylenes, and aryl isothiocyanates undergo hydrothiolation whereas aliphatic isothiocyanates undergo hydroamination. In the presence of a strong base, NaOH for instance, isothiocyanates are exclusively hydrothiolated...