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The Z-selectivity observed in imine and alkene motifs after 5-exo-dig cyclization of propargyl alcohol and isothiocyanate is rare in the literature and this selectivity can be attributed to electronic and steric factors of the imine and alkene motif respectively.

This study presents an efficient procedure for synthesis of 3,4,5‐trisubstituted 3H‐oxazol‐2‐ones and 3,4‐disubstituted (Z)‐oxazolidin‐2‐ones from substituted propargyl alcohols and aryl/alkyl isocyanates in the presence of LiOtBu, a base, and DMF, a solvent. This one‐step, low‐cost and gram scale synthesis exhibits superior atom economy, good to excellent yields, enhanced substrate scope and, high functional group tolerance and uses column chromatography‐free purifications. Further, a product containing bromo substituent was successfully examined for Suzuki coupling with a view to amplifying the complexity of the molecule. Finally, the three component (aniline, Di‐tert‐butyldicarbonate and propargyl alcohol) reaction was demonstrated to get the oxazolon‐2‐ones (3H‐oxazol‐2‐one and oxazolidin‐2‐one).