13053-83-3Relevant academic research and scientific papers
Behavior of free sugar thiosemicarbazones toward heterocyclization reactions
Martins Alho, Miriam A.,D'Accorso, Norma B.
, p. 481 - 488 (2007/10/03)
The heterocyclization reaction on thiosemicarbazones having the D-galacto, D-gluco and D-manno configuration was studied. We applied two different acetylating conditions, and the reaction products obtained were identified, spectroscopically characterized, and conformationally analyzed. Using experimental data, we discuss a possible mechanistic pathway for heterocyclization and evaluate the influence of several factors, including starting material configuration, pH of reaction medium, and reaction time. (C) 2000 Elsevier Science Ltd.
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
