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

[1] 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
V. A. Kataev
S. A. Mesheryakova
E. S. Mesheryakova
T. V. Tyumkina
L. M. Khalilov
V. V. Lazarev
V. V. Kuznetsov
Russian Journal of General Chemistry, 2021, 91 : 785 - 791
[2] Synthesis and structure of hydrazones obtained by the reaction of 2-[6-methyl-2,4-dioxo-1-(thietan-3-yl)-1,2,3,4-tetrahydropyrimidin-3-yl]acetic acide hydrazide with β-dicarbonyl compounds
Meshcheryakova, S. A.
Kataev, V. A.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (05) : 711 - 715
[3] Synthesis and structure of hydrazones obtained by the reaction of 2-[6-methyl-2,4-dioxo-1-(thietan-3-yl)-1,2,3,4-tetrahydropyrimidin-3-yl]acetic acide hydrazide with β-dicarbonyl compounds
S. A. Meshcheryakova
V. A. Kataev
Russian Journal of Organic Chemistry, 2014, 50 : 711 - 715
[4] 2-(2,4-Dichlorophenyl)-N-(1,3-thiazol-2-yl)acetamide
Nayak, Prakash S.
Narayana, B.
Yathirajan, H. S.
Jasinski, Jerry P.
Butcher, Ray J.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O656 - +
[5] 2-(3,4-Dichlorophenyl)-N-(1,3-thiazol-2-yl) acetamide
Nayak, Prakash S.
Narayana, B.
Yathirajan, H. S.
Jasinski, Jerry P.
Butcher, Ray J.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O645 - +
[6] Synthesis of 5-Alkyl-1,3-bis[2-hydroxy-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)propyl]-6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-diones
V. P. Krivonogov
G. G. Kozlova
E. A. Belaya
G. A. Sivkova
L. V. Spirikhin
I. B. Abdrakhmanov
V. V. Plechev
Russian Journal of Organic Chemistry, 2004, 40 : 417 - 420
[7] Synthesis of 5-alkyl-1,3-bis[2-hydroxy-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)propyl]-6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-diones
Krivonogov, VP
Kozlova, GG
Belaya, EA
Sivkova, GA
Spirikhin, LV
Abdrakhmanov, IB
Plechev, VV
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (03) : 417 - 420
[8] Reaction of thietane-containing 2-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)-acetohydrazides with N-phenylmaleimide
S. A. Meshcheryakova
Russian Journal of Organic Chemistry, 2015, 51 : 139 - 140
[9] Reaction of thietane-containing 2-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)-acetohydrazides with N-phenylmaleimide
Meshcheryakova, S. A.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (01) : 139 - 140
[10] N-(6-amino-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-N-(β-D-glucopyranosyl)acetamide
Low, JN
Molina, S
Nogueras, M
Sánchez, A
Cobo, J
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2000, 56 : E420 - E420

← 1 2 3 4 5 →