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Thioaurones were prepared one pot in high yield by the treatment of N,N-diethyl-2(methylsulfanyl)arylamides with LDA and an aromatic aldehyde through directed orthometalation. Heating the thioaurones derived from cinnamaldehyde above 200 oC resulted in [1]benzothieno[3,2-b]pyrans. Treatment of N,N-diethyl-2-(methylsulfanyl)benzamide and crotonaldehyde gave 4-(methylsulfanyl)benzothieno[3,2,-b]pyran via conjugate nucleophilic addition and ring closure in one pot. A possible mechanistic pathway is discussed.

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Synthetic studies in sulfur heterocycles. One-pot synthesis of “thioaurones” and their conversion into [1]benzothieno[3,2-b]pyrans via tandem reactions