Quantum chemical studies of pyrimidin-4-ones Part 6. On peculiarities of the reactions with nitrating agents of some carboxylic acids of the thieno[2,3-d]pyrimidin-4-one series and their esters
- Авторлар: Mamarakhmonov M.1, Belen’kii L.2, Chuvylkin N.2, Asqarov I.1
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Мекемелер:
- Z. M. Babur Andijan State University
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- Шығарылым: Том 65, № 3 (2016)
- Беттер: 654-657
- Бөлім: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/237430
- DOI: https://doi.org/10.1007/s11172-016-1351-x
- ID: 237430
Дәйексөз келтіру
Аннотация
Quantum chemical calculations of the energies, electronic structures, and molecular geometries of 5-methyl-, 2,5-dimethyl-, 3,5-dimethyl-, and 2,3,5-trimethyl-4-oxothieno[2,3-d]pyrimidine-6-carboxylic acids; 5-methyland 3,5-dimethyl-2,4-dioxothieno[2,3-d]pyrimidine6-carboxylic acids; 5-methyland 3,5-dimethyl-4-oxo-2-thiothieno[2,3-d]pyrimidine-6-carboxylic acids; and their ethyl esters were performed in terms of the HF and DFT (B3LYP) approximations in the 3-21G basis set. The reactions routes with nitrating agents were examined, and the factors governing the direction of the reactions, the probability of their occurrence were determined. Selective ipso-substitution of the 5-methyl group by the nitro group at the C(5) atom of the thiophene fragment is hindered for all compounds studied. The reasons for the unfavorable ipso-substitution were discussed taking into account effects of solvents and substituents in positions 2, 3, and 6 of 6-carboxyand 6-ethoxycarbonyl-substituted thieno[2,3-d]pyrimidin-4-ones.
Авторлар туралы
M. Mamarakhmonov
Z. M. Babur Andijan State University
Хат алмасуға жауапты Автор.
Email: muhamatdin@mail.ru
Өзбекстан, 129 ul. Universitetskaya, Andijan, 170100
L. Belen’kii
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Хат алмасуға жауапты Автор.
Email: libel31@mail.ru
Ресей, 47 Leninsky prosp., Moscow, 119991
N. Chuvylkin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: libel31@mail.ru
Ресей, 47 Leninsky prosp., Moscow, 119991
I. Asqarov
Z. M. Babur Andijan State University
Email: libel31@mail.ru
Өзбекстан, 129 ul. Universitetskaya, Andijan, 170100