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

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Abstract

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, 4H-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.

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Authors and Affiliations

  1. Ganja State University, AZ-2000, Gandja, Azerbaijan

    G. E. Allahverdiyeva

  2. Baku State University, AZ-1148, Baku, Azerbaijan

    V. M. Ismailov, I. A. Mamedov & N. N. Yusubov

Authors
  1. G. E. Allahverdiyeva
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  2. V. M. Ismailov
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  3. I. A. Mamedov
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  4. N. N. Yusubov
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Correspondence to N. N. Yusubov.

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Allahverdiyeva, G.E., Ismailov, V.M., Mamedov, I.A. et al. Reactions of Triethyl Phosphonoacetate, Bromoacetaldehyde Diethyl Acetal, and (Diethoxyphosphoryl)acetaldehyde with Thiourea and (Thio)semicarbazide. Russ J Gen Chem 93, 1064–1068 (2023). https://doi.org/10.1134/S1070363223050067

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