Synthesis of 3-Thia-1-dethiacephems via Regioselective Iodocyclization Reaction

Abstract

The key N-homopropargylthiourea intermediates, N-substituted 2-oxo-4-propargylazetidine-1-carbothioamides, were prepared by the reaction of a 4-propargylazetidin-2-one with isothiocyanates. Bicyclic β-lactams, i.e. 3-thia-1-dethiacephems, were prepared via highly regioselective iodocyclization reaction of N-substituted 2-oxo-4-propargylazetidine-1-carbothioamides with molecular iodine at room temperature in moderate to excellent yields. A variety of functional groups were well tolerated under the reaction conditions.

Key words

β-lactams - iodocyclization - thiourea - 3-thia-1-dethiacephems - regioselective

• References and Notes

• 1 Affiliated to Savitribai Phule Pune University (formerly University of Pune).

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