From Chemistry Towards Technology Step-By-Step From Chemistry Towards Technology Step-By-Step От химии к технологии шаг за шагом 2782-1900 83099 10.52957/27821900_2021_01_157 Научные статьи Scientific articles Научные статьи Quantum chemical modeling of the formation of 3-phenyl-5-methyl-1,2,4-oxadiazole Quantum chemical modeling of the formation of 3-phenyl-5-methyl-1,2,4-oxadiazole Кофанов Евгений Романович Kofanov Evgeny Romanovich

доктор химических наук;

doctor of chemical sciences;

 Ярославский государственный технический университет Yaroslavl State Technical University 23 03 2021 23 03 2021 2 1 157 160 22 01 2021 10 03 2021 https://chemintech.ru/en/nauka/article/83099/view

A quantum chemical simulation of the formation of 3-phenyl-5-methyl-1,2,4-oxadiazole was performed. The energy of intermediate particles and the transition state is calculated. The directions of acylation of amidoxime are considered.

A quantum chemical simulation of the formation of 3-phenyl-5-methyl-1,2,4-oxadiazole was performed. The energy of intermediate particles and the transition state is calculated. The directions of acylation of amidoxime are considered.

 1 2 4-oxadiazole acylation cyclization quantum chemical modeling

Sharonova T., Pankrateva V., Savko P., Baykov S., Shetnev A. Facile room-temperature assembly of the 1,2,4-oxadiazole core from readily available amidoximes and carboxylic acids. Tetrahedron Letters. 2018. V. 59. P. 2824-2827. URL: https://doi.org/10.1016/j.tetlet.2018.06.019. Sharonova T., Pankrateva V., Savko P., Baykov S., Shetnev A. Facile room-temperature assembly of the 1,2,4-oxadiazole core from readily available amidoximes and carboxylic acids. Tetrahedron Letters. 2018. V. 59. P. 2824-2827. URL: https://doi.org/10.1016/j.tetlet.2018.06.019. Baykov S., Sharonova T., Shetnev A., Rozhkov S., Kalinin S., Smirnov A.V. The first one-pot ambient-temperature synthesis of 1,2,4-oxadiazoles from amidoximes and carboxylic acid esters. Tetrahedron Letters. 2017. V. 73. P. 945-951. URL: https://doi.org/10.1016/j.tet.2017.01.007. Baykov S., Sharonova T., Shetnev A., Rozhkov S., Kalinin S., Smirnov A.V. The first one-pot ambient-temperature synthesis of 1,2,4-oxadiazoles from amidoximes and carboxylic acid esters. Tetrahedron Letters. 2017. V. 73. P. 945-951. URL: https://doi.org/10.1016/j.tet.2017.01.007. Wang Y, Miller R.L., Sauer D.R., Djuric S.W. Rapid and Efficient Synthesis of 1,2,4-Oxadiazoles Utilizing Polymer-Supported Reagents under Microwave Heating. Tetrahedron Letters. 2005. V. 7. P. 925-928. URL: https: //doi.org/10.1021/ol050007r. Wang Y, Miller R.L., Sauer D.R., Djuric S.W. Rapid and Efficient Synthesis of 1,2,4-Oxadiazoles Utilizing Polymer-Supported Reagents under Microwave Heating. Tetrahedron Letters. 2005. V. 7. P. 925-928. URL: https: //doi.org/10.1021/ol050007r. Tarasenko M., Duderin N., Sharonova T., Baykov S., Shetnev A. Room-temperature synthesis of harmaceutically important carboxylic acids bearing the 1,2,4-oxadiazole moiety. Tetrahedron Letters. 2017. V. 58. P. 3672-3677. URL: https://doi.org/10.1016/j.tetlet.2017.08.020. Tarasenko M., Duderin N., Sharonova T., Baykov S., Shetnev A. Room-temperature synthesis of harmaceutically important carboxylic acids bearing the 1,2,4-oxadiazole moiety. Tetrahedron Letters. 2017. V. 58. P. 3672-3677. URL: https://doi.org/10.1016/j.tetlet.2017.08.020. Tamura M., Ise Y., Okajima Y., Nishiwaki N., Ariga M. Facile Synthesis of 3-Carbamoyl-1,2,4-Oxadiazoles. Synthesis. 2006. P. 3453-3461. URL: https://doi.org/10.1055/s-2006-950210. Tamura M., Ise Y., Okajima Y., Nishiwaki N., Ariga M. Facile Synthesis of 3-Carbamoyl-1,2,4-Oxadiazoles. Synthesis. 2006. P. 3453-3461. URL: https://doi.org/10.1055/s-2006-950210. Amarasinghe K.K.D., Maier M.B., Srivastava A., Gray J.L. One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acid esters and amidoximes using potassium carbonate. Tetrahedron Letters. 2006. Vol. 47 P. 3629-3631. URL: https://doi.org/10.1016/j.tetlet.2006.03.155. Amarasinghe K.K.D., Maier M.B., Srivastava A., Gray J.L. One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acid esters and amidoximes using potassium carbonate. Tetrahedron Letters. 2006. Vol. 47 P. 3629-3631. URL: https://doi.org/10.1016/j.tetlet.2006.03.155. Du W., Truong Q., Qi H., Guo Y., Chobanian H.R., Hagmann W.K., Hale J.J. A one-pot synthesis of 3-substituted-5-carbonylmethyl-1,2,4-oxadiazoles from β-keto esters and amidoximes under solvent-free conditions. Tetrahedron Letters. 2007. V. 48. P. 2231-2235. URL: https://doi.org/10.1016/j.tetlet.2007.02.005 Du W., Truong Q., Qi H., Guo Y., Chobanian H.R., Hagmann W.K., Hale J.J. A one-pot synthesis of 3-substituted-5-carbonylmethyl-1,2,4-oxadiazoles from β-keto esters and amidoximes under solvent-free conditions. Tetrahedron Letters. 2007. V. 48. P. 2231-2235. URL: https://doi.org/10.1016/j.tetlet.2007.02.005 Lin Y., Lang S., Lovell M.F., Perkinson N.A. New synthesis of 1,2,4-triazoles and 1,2,4-oxadiazoles. Journal of Organic Chemistry. 1979. V. 44. P. 4160-4164. URL: https://doi.org/10.1021/jo01337a031 Lin Y., Lang S., Lovell M.F., Perkinson N.A. New synthesis of 1,2,4-triazoles and 1,2,4-oxadiazoles. Journal of Organic Chemistry. 1979. V. 44. P. 4160-4164. URL: https://doi.org/10.1021/jo01337a031 Neidlein R., Li S. Syntheses of 1,2,4-oxadiazole substituted pyrazole, isoxazole and pyrimidine heterocycles. Journal of Heterocyclic Chemistry. 1996. V. 33. P.1943-1949. URL: https://doi.org/10.1002/jhet.5570330663 Neidlein R., Li S. Syntheses of 1,2,4-oxadiazole substituted pyrazole, isoxazole and pyrimidine heterocycles. Journal of Heterocyclic Chemistry. 1996. V. 33. P.1943-1949. URL: https://doi.org/10.1002/jhet.5570330663 Karunnaya M.V., Sosnina V.V., Krasovskaya G.G., Danilova A.S., Kofanov E.R. Sintez 3-(3-nitrofenil)-5-stiril-1,2,4-oksadiazola. Izvestiya vuzov. Khimiya i khim. Tekhnologiya. 2014. V. 57. N. 12. P. 15-16 (in Russian). Karunnaya M.V., Sosnina V.V., Krasovskaya G.G., Danilova A.S., Kofanov E.R. Sintez 3-(3-nitrofenil)-5-stiril-1,2,4-oksadiazola. Izvestiya vuzov. Khimiya i khim. Tekhnologiya. 2014. V. 57. N. 12. P. 15-16 (in Russian). Tsiulin P.A., Sosnina V.V., Krasovskaya G.G., Danilova A.S., Baikov S.V., Kofanov E.R. Formation and cyclization of N′-(benzoyloxy)benzenecarboximidamides. Russian Journal of Organic Chemistry. 2011. V. 47. N 12. P. 1874–1877. URL: https://link.springer.com/article/10.1134%2FS10704280111201531877. DOI: 10.1134/s1070428011120153. Tsiulin P.A., Sosnina V.V., Krasovskaya G.G., Danilova A.S., Baikov S.V., Kofanov E.R. Formation and cyclization of N′-(benzoyloxy)benzenecarboximidamides. Russian Journal of Organic Chemistry. 2011. V. 47. N 12. P. 1874–1877. URL: https://link.springer.com/article/10.1134%2FS10704280111201531877. DOI: 10.1134/s1070428011120153. Rajendra M. Srivastava, Wagner M. Faustio, Ira M. Brin. Semi-empirical (PM3 and AM1) and ab initio molecular orbital calculations of 1,2,4-oxadiazoles, 4,5-dihydro-1,2,4-oxadiazoles and 4,4-di-n-butyl-2-phenylbenzo-1,3-oxazine. Journal of Molecular Structure (Theochem). V. 640(2003). P. 49–56. URL: https:// doi.org /10.1016/S0166-1280(03)00511-6. Rajendra M. Srivastava, Wagner M. Faustio, Ira M. Brin. Semi-empirical (PM3 and AM1) and ab initio molecular orbital calculations of 1,2,4-oxadiazoles, 4,5-dihydro-1,2,4-oxadiazoles and 4,4-di-n-butyl-2-phenylbenzo-1,3-oxazine. Journal of Molecular Structure (Theochem). V. 640(2003). P. 49–56. URL: https:// doi.org /10.1016/S0166-1280(03)00511-6. David J. Giesen, Gregory D. Hawkins, Daniel A. Liotard, Christopher J. Cramer, Donald G. Truhlar. A universal model for the quantum mechanical calculation of free energies of solvation in non-aqueous solvents. Theoretical Chemistry Accounts. 1997. V. 98. P. 85-109. URL: https://doi.org/10.1007/s002140050283. David J. Giesen, Gregory D. Hawkins, Daniel A. Liotard, Christopher J. Cramer, Donald G. Truhlar. A universal model for the quantum mechanical calculation of free energies of solvation in non-aqueous solvents. Theoretical Chemistry Accounts. 1997. V. 98. P. 85-109. URL: https://doi.org/10.1007/s002140050283. Cramer C.J., Truhlar D.G. AM1-SM2 and PM3-SM3 parameterized SCF solvation models for free energies in aqueous solution. Journal of Computer-Aided Molecular Design. 1992. V. 6. P. 629-666. URL: https://doi.org /10.1007/BF00126219. Cramer C.J., Truhlar D.G. AM1-SM2 and PM3-SM3 parameterized SCF solvation models for free energies in aqueous solution. Journal of Computer-Aided Molecular Design. 1992. V. 6. P. 629-666. URL: https://doi.org /10.1007/BF00126219. Daniel A. Liotard, Gregory D. Hawkin, Gillian C. Lynch, Christopher J. Cramer, Donald G. Truhlar. Improved methods for semiempirical solvation models. Journal of Computational Chemistry. 1995. V. 16. N 4. P. 422-440. URL: https://doi.org/10.1002/jcc.540160405. Daniel A. Liotard, Gregory D. Hawkin, Gillian C. Lynch, Christopher J. Cramer, Donald G. Truhlar. Improved methods for semiempirical solvation models. Journal of Computational Chemistry. 1995. V. 16. N 4. P. 422-440. URL: https://doi.org/10.1002/jcc.540160405.