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LiAlH4-Induced Thia-Aza-Payne Rearrangement of Functionalized 2-(Thiocyanatomethyl)aziridines into 2-(Aminomethyl)thiiranes as an Entry to 5-(Chloromethyl)thiazolidin-2-ones
Nonactivated 2-(thiocyanatomethyl)aziridines with diverse substitution patterns were deployed as substrates to effect a LiAlH4-promoted thia-aza-Payne rearrangement to provide access to functionalized 2-(aminomethyl) thiiranes in good to excellent yields (78-94 %). The developed strategy involved hydride reduction of the thiocyanato moiety followed by intramolecular aziridine ring opening. Subsequent exposure of the obtained 2-(aminomethyl) episulfide intermediates to triphosgene resulted in the formation of 5-(chloromethyl)thiazolidin-2-ones.
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Reference:
Thiazolidine – Wikipedia,
,Thiazolidine – ScienceDirect.com