15059-36-6Relevant articles and documents
Cyclization Reactions of Tricarbonylmethane Thiosemicarbazones: Formation of 1,3,4-Thiadiazole Derivatives with Concomitant C-C Bond Cleavage
Somogyi, Laszlo
, p. 721 - 724 (2007/10/02)
Under acylating conditions 3-acetyl-4-hydroxy-2H-pyran-2-one thiosemicarbazones (1a, b and 2a, b) are transformed into 2-(acylamino)-5-methyl-1,3,4-thiadiazoles 3b, c, e, f and 2H-pyran-2-ones 1c and 2c via C-C bond cleavage.Similarly, the reaction of 1b with RCO2H/EtOH (R = Me, Et) affords 2-anilino-5-methyl-1,3,4-thiadiazole (3d) and triacetic acid lactone 1c.Upon treatment with Ac2O/Et3N the dehydroacetic acid derivative 1b is transformed into the thiadiazoline 4, while the benzo derivative 2b is converted into thiadiazole 3e and 4-acetoxycoumarin (2c). - Key Words: 2H-Pyran-2-ones / Coumarins / 1,3,4-Thiadiazoles / Thiosemicarbazones