Ethoxycarbonyl isothiocyanate reacted with phenols in a nitromethane solution of aluminum chloride to yield the appropriate 4-hydroxy-N-ethoxycarbonylthiobenzamides. In the reaction with dinucleophiles they gave heterocyclic compounds which were subsequently functionalized on the hydroxy group. The reaction of p-hydroxythiobenzamides with carbamoyl chloride, chlorides of α,β-unsaturated carboxylic acids, and isocyanates yielded the corresponding O-acylated products.
The reaction of isothiocyanates with in situ generated carbanions of , -unsaturated ketones yielded , -unsaturated keto thioamides which in the reaction with acids or bases cyclized to give 2,6-disubstituted thiopyran-4-ones and in the reaction with -bromoesters gave thiazolidin-4-one derivatives. The thiopyran-4-ones reacted with , -unsaturated aldehydes to yield tetrahydrothiopyran [2,3-b]pyridin-4-ones, while thioanilides were formed in the reaction with phenyl isothiocyanate.
The reaction of isothiocyanates with in situ generated carbanions of α,β‐unsaturated ketones yielded α,β‐unsaturated keto thioamides which in the reaction with acids or bases cyclized to give 2,6‐disubstituted thiopyran‐4‐ones and in the reaction with α‐bromoesters gave thiazolidin‐4‐one derivatives. The thiopyran‐4‐ones reacted with α,β‐unsaturated aldehydes to yield tetrahydrothiopyran[2,3‐b]pyridin‐4‐ones, while thioanilides were formed in the reaction with phenyl isothiocyanate.
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