ChemInform Abstract: Ring‐Chain and Ring‐Chain‐Ring Tautomerism of Thiocarbonohydrazones

Abstract

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Synthesis and Characterization of Novel N‐Alkylamine‐ and N‐Cycloalkylamine‐Derived 2‐Benzoyl‐N‐aminohydrazinecarbothioamides, 1,3,4‐Thiadiazoles and 1,2,4‐Triazole‐5(4H)thiones

“…The mixture was refluxed for 2 h. Then, the solution was cooled, and the precipitate was filtered off, washed with ice‐cold water, dried, and recrystallized from water ( 4 ) or methanol ( 5 , 6 ). Reaction yields and compounds' characteristics were found to be identical with those described earlier .…”

“…Compounds ( 1 , 2 ) have been already described by Podgornaya and co‐workers , whereas methyl 2,2‐dimethylhydrazinecarbodithioate by Johnston and Gallagher . In the reaction of methyl carbamodithioates with hydrazine hydrate, the appropriate aminohydrazinecarbothioamides ( 4 , 5 , 6 ) were obtained . Then, synthesized aminohydrazinecarbothioamides ( 4 , 5 , 6 ) were treated with the following acid chlorides: benzoyl, 4‐chlorobenzoyl, 4‐fluorobenzoyl, 4‐methoxubenzoyl, and 2‐furoyl.…”

ChemInform Abstract: Synthesis and Characterization of Novel N‐Alkylamine‐ and N‐Cycloalkylamine‐Derived 2‐Benzoyl‐N‐aminohydrazinecarbothioamides, 1,3,4‐Thiadiazoles and 1,2,4‐Triazole‐5(4H)thiones.

“…General method for the synthesis of 1,3,4-thiadiazoles (17)(18)(19)(20)(21)(22)(23)(24). General method for the synthesis of 1,3,4-thiadiazoles (17)(18)(19)(20)(21)(22)(23)(24).…”

“…Obtained hydrazinecarbothioamide derivatives (7-10, 12, 14-16) were cyclized to 2-(N-morpholino, N-piperidino, and N-dimethylamino)-amino-5-phenylo-1,3,4-thiadiazoles (17)(18)(19)(20)(21)(22)(23)(24). Reactions were carried out in concentrated sulfuric acid at 90 C. The cyclization of thiosemicarbazide derivatives in boiling 10% NaOH aqueous solution led to 1,2,4-triazole-5(4H)-thiones (25-33) substituted at N-4 position with N,N-dimethylamine, morpholine, or piperidine.…”

An Update of the Use of Thiocarbohydrazides and Thiosemicarbazides in the Preparation of Heterocycles and Their Biological Importance

“…N ‐Aminohydrazinecarbothioamides 71a – c were synthesized by hydrazinolysis of methyl amino‐carbamodithioates 70a – c (Scheme ). Compounds 70a – c were prepared from reaction of amines with CS 2 followed by methylation using methyl iodide at r.t. as described in Scheme .…”