Reactions of triethyl phosphonoacetate, bromoacetaldehyde diethyl acetal, and (diethoxyphosphoryl)acetaldehyde with thiourea and (thio)semicarbazide
- Autores: Allahverdiyeva G.1, Ismailov V.2, Mamedov I.2, Yusubov N.2
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Afiliações:
- Ganja State University
- Baku State University
- Edição: Volume 93, Nº 5 (2023)
- Páginas: 711-716
- Seção: Articles
- URL: https://journals.rcsi.science/0044-460X/article/view/145047
- DOI: https://doi.org/10.31857/S0044460X23050062
- EDN: https://elibrary.ru/DBUOJE
- ID: 145047
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Resumo
Condensation of thiocarbamide with triethyl phosphonoacetate leads to S -phosphorylated 2-ethoxy-4-oxo3,4,5-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.
Sobre autores
G. Allahverdiyeva
Ganja State University
V. Ismailov
Baku State University
I. Mamedov
Baku State University
N. Yusubov
Baku State University
Email: yniftali@gmail.com
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