0000000000185874
AUTHOR
Francesco Buccheri
ChemInform Abstract: Substituent Effect on Oxidative Cyclization of Aldehyde Thiosemicarbazones with Ferric Chloride.
The reactivity of aldehyde thiosemicarbazones 1 with ferric chloride solutions was examined. When compounds 1 are not substituted on the N-2 nitrogen atom formation of 1,3,4-thiadiazole 3 heterocyclic ring was observed. In contrast 1,2,4-triazoline 4 and/or 1,3,4-thiadiazoline 5 heterocyclic rings were afforded when N-2 nitrogen atom carried a methyl or a phenyl group. The reaction mechanism is also discussed.
A study of the behaviour of 2,4-substituted thiosemicarbazides toward orthoesters: Formation of mesoionic compounds
The reactions beetwen 2,4-disubstituted thiosemicarbazides and orthoesters in refluxing xylene led to the formation of the 1,2,4-triazoline-5-thione ring and to the 1,2,4-triazolium-5-thiolate ring. The formation of the mesoionic componds is due to rearrangement of the easily available 2,4-disubstituted thiosemicarbazides to 1,4-disubstituted thiosemicarbazides under the reaction conditions adopted. This method can be usefully used for the synthesis of mesoionic compounds, especially in the case of the 2-methyl-4-phenylthiosemicarbazide.
ChemInform Abstract: Methylation of 2-Phenylamino-1,3,4-thiadiazole. A Structure Debated.
The true identity of the 4-methyl-5-phenylimino-δ2-1,3,4-thiadiazoline (A) has been demonstrated. The reactions, previously reported in the literature to give A have been repeated and the structure of the compounds obtained has been established.
Oxidative cyclization of some aldehyde semicarbazones induced by metallic salts
The oxidative cyclization of some aldehyde semicarbazones 10 with four different oxidizing agents has been effected. The structure of the semicarbazones and the nature of cyclizing agent affected the rate and yield of cyclization but they did not show any influence on the regiochemistry of reaction. In fact, 1,2,4-triazoline 20 was the only heterocyclic ring obtained by the cyclization reaction.
ChemInform Abstract: Oxidative Cyclization of Some Aldehyde Semicarbazones Induced by Metallic Salts.
The oxidative cyclization of some aldehyde semicarbazones 10 with four different oxidizing agents has been effected. The structure of the semicarbazones and the nature of cyclizing agent affected the rate and yield of cyclization but they did not show any influence on the regiochemistry of reaction. In fact, 1,2,4-triazoline 20 was the only heterocyclic ring obtained by the cyclization reaction.
Substituent effect on oxidative cyclization of aldehyde thiosemicarbazones with ferric chloride
The reactivity of aldehyde thiosemicarbazones 1 with ferric chloride solutions was examined. When compounds 1 are not substituted on the N-2 nitrogen atom formation of 1,3,4-thiadiazole 3 heterocyclic ring was observed. In contrast 1,2,4-triazoline 4 and/or 1,3,4-thiadiazoline 5 heterocyclic rings were afforded when N-2 nitrogen atom carried a methyl or a phenyl group. The reaction mechanism is also discussed.
Methylation of 2-phenylamino-1,3,4-thiadiazole. A structure debated
The true identity of the 4-methyl-5-phenylimino-δ2-1,3,4-thiadiazoline (A) has been demonstrated. The reactions, previously reported in the literature to give A have been repeated and the structure of the compounds obtained has been established.
Photochemical cyclization of some aldehyde thiosemicarbazones
The photochemical behaviour of some substituted aldehyde thiosemicarbazones 1a-k has been investigated in methanol at 254 nm. Thiosemicarbazones of glyoxil methyl ester 1a-f cyclized to furnish the 3-thioxo- 1,2,4-triazin-5-one 2 ring system. The remaining thiosemicarbazones 1g-j gave 1,2,4-triazoline 4 derivatives.
ChemInform Abstract: Photochemical Cyclization of Some Aldehyde Thiosemicarbazones.
The photochemical behaviour of some substituted aldehyde thiosemicarbazones 1a-k has been investigated in methanol at 254 nm. Thiosemicarbazones of glyoxil methyl ester 1a-f cyclized to furnish the 3-thioxo- 1,2,4-triazin-5-one 2 ring system. The remaining thiosemicarbazones 1g-j gave 1,2,4-triazoline 4 derivatives.