Synthesis of ThioporpholineDerivatives via Multicomponent Reaction of Terminal Alkynes, Isothiocyanates, and Aziridines

Document Type : Research Article


Young Research and Elite Club, Buin Zahra Branch, Islamic Azad University, Buin Zahra, Iran


Copper acetylide was reacted with isothiocyanates and aziridines to form 1,4-thiomorpholine derivatives. Reaction outcome depends highly on the reaction conditions and the particular solvent employed. Optimum conditions are developed using copper triflate in DMSOat70 ˚C. Both the alkyl- and aryl- substituted aziridines and terminal alkynes were tolerated. Variation on isothiocyanates structure did not affect the reaction efficiency in an appreciable manner.Oxirane derivatives exhibited lower reactivity than that aziridines. Alkyl aziridines afforded terminal-attacked products while phenyl aziridines gave benzylic-attacked products.Aziridines derived from cyclopentene did not participate in this transformation.


Main Subjects

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