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.

The LiAlH₄-promoted thia-aza-Payne rearrangement of nonactivated 2-(thiocyanatomethyl)aziridines provides access to functionalized 2-(aminomethyl)thiiranes. The strategy is based on hydride reduction of the thiocyanato moiety followed by intramolecular aziridine ring opening. Subsequent exposure of the obtained 2-(aminomethyl)episulfides to triphosgene gives 5-(chloromethyl)thiazolidin-2-ones.

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