Synthesis, Structure, and Conformational Analysis of N-(2,4-Dichlorophenyl)-2-[6-methyl-2,4-dioxo-3-(thietan-3-yl)-1,2,3,4-tetrahydropyrimidine-1-yl]acetamide

被引：4

作者：

Kataev, V. A. ^{[1
]}

Mesheryakova, S. A. ^{[1
]}

Mesheryakova, E. S. ^{[2
]}

Tyumkina, T., V ^{[2
]}

Khalilov, L. M. ^{[2
]}

Lazarev, V. V. ^{[3
]}

Kuznetsov, V. V. ^{[3
,4
]}

机构：

[1] Bashkirian State Med Univ, Ufa 450008, Russia

[2] Russian Acad Sci, Inst Petrochem & Catalysis, Ufa 450075, Russia

[3] Ufa State Aviat Tech Univ, Ufa 450008, Russia

[4] Ufa State Petr Technol Univ, Ufa 450062, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2021年 / 91卷 / 05期

关键词：

6-methyl-3-(thietan-3-yl)uracil; 6-methyluracil derivatives; thietanes; computer simulation; cluster model; GAUSSIAN-BASIS SETS;

D O I：

10.1134/S1070363221050054

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of 6-methyluracil with 2-chloromethyltiiran affords 6-methyl-3-(thietan-3-yl)uracil. Its subsequent reaction with N-(2,6-dichlorophenyl)-2-chloroaceta-mide resulted in N-(2,4-dichlorophenyl)-2-[6-methyl-2,4-dioxo-3-(thietan-3-yl)-1,2,3,4-tetrahydropyrimidin-1-yl]acetamide, proved by X-ray analysis, NMR and IR spectroscopy. Computer modeling at the PBE/3 zeta, PBE/cc-pVDZ and PBE/SV(P) levels showed that its conformational behavior is determined by internal rotation of the thietanyl group both in the gas phase and in chloroform or dimethyl sulfoxide solutions.

引用

页码：785 / 791

页数：7

共 50 条

[21] N-Cyclopropyl-N-[2-(2,4-difluorophenyl)-2-hydroxy-1-(1H-1,2,4-triazol-1-yl)propyl]-2-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetamide dichloromethane 0.62-solvate
Wang, Nan
Guo, Huan-Mei
Hou, Gui-Ge
Hu, Xin-Yue
Meng, Qing-Guo
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2464 - U1459
[22] N-(3,4-Dichlorophenyl)-2,4-dimethylbenzenesulfonamide
Gowda, B. Thimme
Foro, Sabine
Nirmala, P. G.
Fuess, Hartmut
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1976 - U3986
[23] SYNTHESIS AND ANTIMYCOTIC ACTIVITY OF (BENZO[B]THIENYL)METHYL ETHERS OF 1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)ETHANOL AND OF (Z)-1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)ETHANONE OXIME
RAGA, MM
MORENOMANAS, M
CUBERES, MR
PALACIN, C
CASTELLO, JM
ORTIZ, JA
ARZNEIMITTEL-FORSCHUNG/DRUG RESEARCH, 1992, 42-1 (5A): : 691 - 694
[24] Alkylation of 2-(2,4-dichlorophenyl)-3-cyano-6-methyl-4-(1H-1,2,4-triazol-1-yl)methylpyridine at the methylene group
Zhu, Yan
Cai, Zhengyan
Hao, Qun
Zhou, Weicheng
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (08) : 564 - 569
[25] 4-(2,4-dichlorophenyl)-2-(1H-indol-3-yl)-6-methoxypyridine-3,5-dicarbonitrile
Ramesh, P.
Subbiahpandi, A.
Thirumurugan, P.
Perumal, P. T.
Ponnuswamy, M. N.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O1892 - U3475
[26] Alkylation of 2-(2,4-dichlorophenyl)-3-cyano-6-methyl-4-(1H-1,2,4-triazol-1-yl)methylpyridine at the methylene group
Yan Zhu
Zhengyan Cai
Qun Hao
Weicheng Zhou
Chemistry of Heterocyclic Compounds, 2016, 52 : 564 - 569
[27] Aminomethylation of 6-methyl-1-(thietan-3-yl)pyrimidine-2,4(1H,3H)-dione
Meshcheryakova, S. A.
Kataev, V. A.
Munasipova, D. A.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (03) : 422 - 424
[28] A highly facile approach to the synthesis of novel 2-(3-benzyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-N-phenylacetamides
Novikov, Mikhail S.
Babkov, Denis A.
Paramonova, Maria P.
Chizhov, Alexander O.
Khandazhinskaya, Anastasia L.
Seley-Radtke, Katherine L.
TETRAHEDRON LETTERS, 2013, 54 (06) : 576 - 578
[29] 3-[2-(2,4-Dichlorophenyl)vinyl]-2-methyl-1-phenylsulfonyl-1H-indole
Ganesh, VK
Yogavel, M
Velmurugan, D
Raj, SSS
Fun, HK
Kannadasan, S
Srinivasan, PC
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2003, 59 : O703 - O705
[30] SYNTHESIS AND ANTIMONOAMINOOXIDATIVE ACTIVITY OF 1-(2,4-DIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE-6-CARBONYL)-2-(SUBSTITUTED BENZYL)HYDRAZINES
VAINILAVICHYUS, PI
MYAKUSHKENE, GD
LAUTSYUVENE, NDI
ROCHKA, VSM
SAVITSKENE, RY
KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1989, 23 (03): : 287 - 290

← 1 2 3 4 5 →