Abstract
Quantum chemical calculations of energies, electronic structures, and molecular geometries of 3,5,6-trimethylthieno[2,3-d]pyrimidin-4-one (1), tricyclic 2,3-tri-, 2,3-tetra-, and 2,3-pentamethylene-substituted 5,6-dimethylthieno[2,3-d]pyrimidin-4-ones (2—4), carboxylic acids 5—8 resulting from oxidation of compounds 1—4 at the methyl group in position 5 of thienopyrimidine, methyl esters of these acids (9—12), and products of ipso-nitration of esters (13—16) were performed in terms of the HF and DFT (B3LYP) approximations with the 3-21G basis set. Also, calculations for mixed anhydrides of nitric acid and carboxylic acids 17—20 were carried out. The possible causes of differences in the behaviors of 3-unsubstituted and 3-substituted thieno[2,3-d]pyrimidin-4-ones were discussed.
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M. Kh. Mamarakhmonov, L. I. Belen´kii, N. D. Chuvylkin, M. A. Ashirmatov, B. Zh. Elmuradov, Kh. M. Shakhidoyatov, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 1986 [Izv. Akad. Nauk. Ser. Khim., 2014, 1986].
M. Shodiyev, B. A. Urakov, N. I. Kurkarramov, Kh. M. Shakhidoyatov, Chem. Heterocycl. Compd. (Engl. Transl.), 1993, 29, 1358 [Khim. Geterotsikl. Soedin., 1993, 1574].
B. Zh. Elmuradov, Kh. A. Bozorov, A. Zh. Kurbanbayeva, I. S. Ortikov, Kh. M. Bobakulov, N. D. Abdullayev, A. Yili, H. A. Aisa, Kh. M. Shakhidoyatov, Am. Chem. Sci. J., 2013, 3, 364.
Org. Synth., 1955, Coll. Vol. 3, p. 820.
E. S. Besidskii, G. A. Golubeva, L. A. Sviridova, Chem. Heterocycl. Compd. (Engl. Transl.), 1985, 21, 782 [Khim. Geterotsikl. Soedin., 1985, 941].
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burrant, S. S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. S. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Menucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Peterson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malik, A. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. V. Gill, B. Johnson, W. Heng, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A. 5, Gaussian Inc., Pittsburgh (PA), 1998.
K. Schofield, Aromatic Nitration, Cambridge Univ. Press, 1980, p. 199.
I. N. Nazarov, N. V. Kuznetsov, A. V. Semenovskii, Dokl. Akad. Nauk SSSR, 1954, 99, 1003 [Dokl. Chem. (Engl. Transl.), 1954, 99].
Y. Ogata, in Oxidation in Organic Chemistry C, Ed. W. S. Trahanovsky, Academic Press, New York, 1978, Ch. IV, p. 298–307.
D. V. Nightingale, Chem. Rev., 1947, 40, 117.
D. A. Singleton, S. R. Merrigan, B. J. Kim, P. Beak, L. M. Phillips, J. K. Lee, J. Am. Chem. Soc., 2000, 122, 3296.
X. Cheng, J. Wang, K. Tang, Y. Lin, Ch. Lin, Chem. Phys. Lett., 2010, 496, 136.
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Dedicated to Academician of the Russian Academy of Sciences V. I. Minkin on the occasion of his 80th birthday.
For Part 4, see Ref. 1.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0534—0539, March, 2015.
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Mamarakhmonov, M.K., Belen´kii, L.I., Chuvylkin, N.D. et al. Quantum chemical studies of pyrimidin-4-ones. Russ Chem Bull 64, 534–539 (2015). https://doi.org/10.1007/s11172-015-0897-3
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DOI: https://doi.org/10.1007/s11172-015-0897-3