Synthesis of 4-Acyl-2-(acylamino)-Δ2-1,3,4-thiadiazolines and 4-Acyl-2-amino-Δ2-1,3,4-thiadiazolines by Acylation of Thiosemicarbazones

Article abstract of DOI:10.1021/jo01296a025

Acylation of aldehyde and ketone thiosemicarbazones (2) with acid anhydrides or acid chlorides gave 4-acyl-2-(acylamino)-Δ²-1,3,4-thiadiazolines (3) in good yields.Treatment of 3 with hydrazine hydrate furnished the 2-amino derivatives (4).The 4-methylthiosemicarbazone of benzaldehyde underwent a similar cyclization with acetic anhydride to furnish the corresponding 2-(acetylmethylamino)thiadiazoline.