Reactions of Triethyl Phosphonoacetate, Bromoacetaldehyde Diethyl Acetal, and (Diethoxyphosphoryl)acetaldehyde with Thiourea and (Thio)semicarbazide

Condensation of thiocarbamide with triethyl phosphonoacetate leads to S -phosphorylated 2-ethoxy-4-oxo-3,4,5-trihydro-1,5,2-diazaphosphinine-2-oxide, an isostere of thiobarbiturate. Under similar conditions, triethyl phosphonoacetate reacts with semicarbazide with the intermediate formation of 2-(di...

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Bibliographic Details
Published in:Russian journal of general chemistry 2023-05, Vol.93 (5), p.1064-1068
Main Authors: Allahverdiyeva, G. E., Ismailov, V. M., Mamedov, I. A., Yusubov, N. N.
Format: Article
Language:English
Subjects:
Acetaldehyde
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Cleavage
Condensates
Hydrazines
Thiosemicarbazides
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Summary:Condensation of thiocarbamide with triethyl phosphonoacetate leads to S -phosphorylated 2-ethoxy-4-oxo-3,4,5-trihydro-1,5,2-diazaphosphinine-2-oxide, an isostere of thiobarbiturate. Under similar conditions, triethyl phosphonoacetate reacts with semicarbazide with the intermediate formation of 2-(diethoxyphosphorylacetyl)hydrazine-1-carboxamide, which forms a triazine upon cleavage of the P–C bond and 1,2,3-phosphadiazole upon cleavage of the C–N bond. Under analogous conditions, the condensation of triethyl phosphonoacetate with thiosemicarbazide proceeds with cleavage of the Р–С bond and heterocyclization with the formation of the 1,3,4-thiadiazine derivative. Upon condensation of bromoacetaldehyde diethyl acetal with thiosemicarbazide, 4 H -1,3,4-thiadiazine-2-amine was formed. (Diethoxyphosphoryl)acetaldehyde reacts with thiosemicarbazide under the same conditions in a ratio of 1 : 2, forming a linear product, thiophosphatoiminohydrazone of (diethoxyphosphoryl)acetaldehyde.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363223050067