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-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.

About the authors

G. E Allahverdiyeva

Ganja State University

V. M Ismailov

Baku State University

I. A Mamedov

Baku State University

N. N Yusubov

Baku State University

Email: yniftali@gmail.com

References

  1. Diel P., Maier L. // Phosphorus, Sulfur, Silicon, Relat. Elem. 1988. Vol. 36. P. 85. doi: 10.1080/03086648808079002
  2. Kafarski P., Lejczak B. // Phosphorus, Sulfur, Silicon, Relat. Elem. 1991. Vol. 63. P. 193. doi: 10.1080/104265091080029443
  3. Antipin I.S., Stoikov I.I., Konovalov A.I. // Phosphorus, Sulfur, Silicon, Relat. Elem. 1999. Vol. 144. P. 347. doi: 10.1080/10426509908546252
  4. Ahluwalia V.K., Aggarwae R. // Proc. Indian Nat. Sci. Acad. 1996. Vol. 5. N 5. P. 369.
  5. Матвеева Е.Д., Подругина Т.А., Колесникова И.Н., Присяжной М.В., Каратеев Г.Г., Зефиров Н.С. // Изв. РАН. Cер. хим. 2010. Т. 59. № 2. С. 409
  6. Matveeva E.D., Podrugina T.A., Kolesnikova I.N., Prisyazhnoi M.V., Karateev G.G., Zefirov N.S. // Russ. Chem. Bull. 2010. Vol. 59. N 2. P. 418. doi: 10.1007/s1172-010-0095-2
  7. Матвеева Е.Д., Подругина Т.А., Колесникова И.Н., Зефиров Н.С. // Изв. РАН. Cер. хим. 2010. Т. 59. № 2. С. 403
  8. Matveeva E.D., Podrugina T.A., Kolesnikova I.N., Zefirov N.S. // Russ. Chem. Bull. 2010. Vol. 59. N 2. P. 411. doi: 10.1007/s1172-010-0094-3
  9. Mатвеева Е.Д., Подругина Т.А., Шарутин И.В., Зефиров Н.С. // Изв. РАН. Cер. хим. 2012. Т. 61. № 2. С. 384
  10. Matveeva E.D., Podrugina T.A., Sharution I.V., Zefirov N.S. // Russ. Chem. Bull. 2012. Vol. 61. N 2 P. 386. doi: 10.1007/s11172-012-0054-1
  11. Певзнер Л.М., Ремизов Ю.О., Петров М.Л. // ЖОХ. 2015. T. 85. № 1. С. 67
  12. Pevzner L.M., Remizov Yu.O, Petrov М.L. // Russ. J. Gen. Chem. 2015. Vol. 85. N 1. P. 61. doi: 10.1134/S1070363215010119
  13. Аюбова М.Р., Аллахвердиева Г.Э., Исмаилов В.М. // Молодой ученый. 2020. № 4(94). С. 1.
  14. Pat. US 11547712.2023.B2
  15. Bosch J., Salas M., Amat M., Alvares M., Adrover B. // Tetrahedron. 1991. Vol. 47. N 28. P. 5269. doi: 10.1016/50040-4020(01087138-6
  16. Rabasso N., Fadel A. // Synthesis. 2008. Vol. 15. P. 2353. doi: 10.1055/s-2008-1067130
  17. Соколов В.Б., Аксиненко А.Ю., Горева Т.В., Епишина Т.А., Габрельян А.В., Григорьев В.В. // ЖОХ. 2020. Т. 90. № 1. С. 42
  18. Sokolov V.B., Aksienko A.Yu., Coreva T.V., Epishina T.A., Gabrel'yan A.B., Grigoriev V.V. // Russ. J. Gen. Chem. 2020. Vol. 90. N 1. Р. 32. doi: 10.1134/S1070363220010053
  19. Шабан Радван, Исмаилов В.М., Юсубов Н.Н., Гулиев А.Н. // III Республиканская конференция молодых ученых-химиков. Баку, 1988. C. 196.
  20. Schman T.J. // J. Heterocycl. Chem. 1983. Vol. 20. N 3. Р. 547. doi: 10.1002/jhet.5570200312

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