0000000000185876
AUTHOR
Giuseppe Werber
showing 13 related works from this author
ChemInform Abstract: Substituent Effect on Oxidative Cyclization of Aldehyde Thiosemicarbazones with Ferric Chloride.
2010
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 quantitative study of substituent effects on oxidative cyclization of some 2-methylsubstituted aldehydes. Thiosemicarbazones induced by ferric chlo…
1996
In order to gain further mechanistical information about the cyclization of thiosemicarbazones and thiosemicarbazone-type substrates induced by metallic salts as oxidizing agents, we performed the synthesis of substrates 1a-s and a kinetic study of the oxidative cyclization of 1 to 5-imino-Δ2-1,3,4-thiadiazole 2 and 1,2,4-triazoline-5-thione 3 derivatives induced by methanolic ferric chloride solutions. The results of cyclization were compared to those of corresponding semicarbazones. The kinetic data were analyzed by means of the Hammett's equation and ρ values discussed.
A study of the behaviour of 2,4-substituted thiosemicarbazides toward orthoesters: Formation of mesoionic compounds
1997
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.
A quantitative study of substituent effects on oxidative cyclization of some 2-aryl-substituted aldehyde thiosemicarbazones induced by ferric chlorid…
1999
As a development of our previous work, we performed a kinetic study of the oxidative cyclization reaction of some 2,4-diaryl-substituted aldehyde thiosemicarbazones 1a-n induced by ferric chloride and by cupric perchlorate. The results of cyclization of 1a-n were compared to those of the corresponding 2-methyl derivatives. The kinetic data were analyzed by means of the Hammett's equation.
ChemInform Abstract: Methylation of 2-Phenylamino-1,3,4-thiadiazole. A Structure Debated.
1987
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
1993
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.
2010
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
1991
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
1987
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.
A study of the mechanism of the oxidative cyclization of benzaldehyde semicarbazones induced by cupric perchlorate in acetonitrile
1995
Treatment of benzaldehyde semicarbazones 1a-i with cupric perchlorate in acetonitrile at 40 provided selectively the corresponding 1,2,4-triazolin-5-ones 2a-i. The relative rate constants for 2a-i formation were determined by the competitive method. The results obtained showed that electron-donating substituents (methyl and methoxy) increase the reaction rate, while the reverse was found for electron-withdrawing substituents (chloro and nitro group). The reactivity data are discussed on the grounds of two possible mechanisms.
Photochemical cyclization of some aldehyde thiosemicarbazones
1992
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: A Quantitative Study of Substituent Effects on Oxidative Cyclization of Some 2-Methylsubstituted Aldehydes. Thiosemicarbazones I…
2010
In order to gain further mechanistical information about the cyclization of thiosemicarbazones and thiosemicarbazone-type substrates induced by metallic salts as oxidizing agents, we performed the synthesis of substrates 1a-s and a kinetic study of the oxidative cyclization of 1 to 5-imino-Δ2-1,3,4-thiadiazole 2 and 1,2,4-triazoline-5-thione 3 derivatives induced by methanolic ferric chloride solutions. The results of cyclization were compared to those of corresponding semicarbazones. The kinetic data were analyzed by means of the Hammett's equation and ρ values discussed.
ChemInform Abstract: Photochemical Cyclization of Some Aldehyde Thiosemicarbazones.
2010
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.