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

6-Methyluracil sodium salt reacts with 1,3-bis(3-chloro-2-hydroxypropyl)-6-methyluracils in DMF, yielding products of alkylation at the nitrogen atom in position 3 of the uracil ring.     

Synthesis and crystal structure analysis of 2-(4-methyl-2′-biphenyl)-4-amino-1,2,4-triazole-3-thiol

The bioactive compound 2-(4-methyl-2′-bip-henyl)-4-amino-1,2,4-triazole-3-thiol, F.W. 282.09 was synthesized, characterized by spectroscopic techniques and confirmed by X-ray crystal structure analysis. The title compound crystallizes in monoclinic class under the space group P2₁/c with cell parameters, a=11.273(3) Å, b=17.245(1) Å, c=7.413(1) Å, β=97.742(5)° and Z=4. The structure exhibits inter-molecular hydrogen bonding of the type N–H···S.     

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

Russian Journal of General Chemistry - The reaction of 6-methyluracil with 2-chloromethyltiiran affords 6-methyl-3-(thietan-3-yl)uracil. Its subsequent reaction with...     

Synthesis of 1,3-Bis[3-X-2-(X-acetoxy)propyl]-6-methyl- 1,2,3,4-tetrahydropyrimidine-2,4-diones

A procedure was developed for synthesizing nitrogen-and-sulfur-containing pyrimidine derivatives by reactions of 1,3-bis(3-chloro-2-hydroxypropyl)-6-methyluracil with 1-butanethiol and chloroacetyl chloride, followed by treatment of the resulting 1,3-bis[3-chloro-2-(chloroacetoxy)propyl]-6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione with 1-butanethiol, morpholine, and piperidine. Oxidation of the sulfur-containing products with NaIO₄ gave the corresponding sulfoxides.     

Synthesis and Crystal Structure of N-[4-(4-Methyl-phenylsulfamoyl)-phenyl]-4-methyl-1,2,3-thiadiazole-5-carboxamide

The crystal structure of the title compound (C17H16N4O3S2, Mr = 388.46) has been determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/c with a = 13.688(2), b = 16.704(3), c = 8.3308(12) , β = 99.474(6)o, V = 1878.8(5) 3, Mr = 388.46, Z = 4, Dc = 1.373 g/cm3, μ = 0.308 mm–1, F(000) = 808, R = 0.0389 and wR = 0.0917. X-ray analysis reveals that the crystal structure involves intermolecular N–H…O and N–H…N hydrogen bonds, which link the molecules into a layer parallel to the ac plane.     

(Z)-1-[2-(Triarylstannyl)vinyl]-1-cycloheptanols: Synthesis, characterization, halodemetallation and crystal structures

The synthesis and characterization by ¹H, ¹³C, ¹¹⁹Sn NMR and ¹¹⁹Sn Mössbauer spectroscopy of (Z)-1-[2-(triphenylstannyl)vinyl]-1-cycloheptanol,

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(1), and (Z)-1-[2-tri-p-tolylstannyl)vinyl-1-cycloheptanol,

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(2), are described, together with their halodemetallation by I₂, Br₂ and ICIl to yield derivatives of the types

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(Ar = phenyl or p-tolyl, N = 1, 2; X = I, Br, Cl, respectively). The solid-state structures of four compounds have been determined by X-ray diffraction analysis. In the crystals of

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(1) and

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(2) the Sn atom has a tetrahedral geometry distorted towards trigonal bipyramid as a consequence of a close intramolecular contact with the hydroxyl O(1) atom of 2.742(3) Å and 2.768(3) Å, respectively. A trigonal bipyramidal geometry is found in

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(12) and

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(4), in which significant Sn---O(1) interactions are noted [2.437(8) Å and 2.407(8) Å, respectively].     

Synthesis,crystal and molecular structure of 2-(3-chloropropyl)-6-methyl-4-phenylquinazoline 3-oxide

The acylation of the syn isomer of the oxime of 2-amino-5-methylbenzophenone with 4-chlorobutyryl chloride gives a mixture of the anti isomer of the 4-chlorobutyryloximine of 2-(4-chlorobutyryl)amino-5-methylbenzophenone and 2-(3-chloropropyl)-6-methyl-4-phenylquinazoline 3-oxide. The crystal and molecular structure of this oxide was established by X-ray diffraction structural analysis. The molecule is planar. The electron impact fragmentation of 2-(3-chloropropyl)-6-methyl-4-phenylquinazoline 3-oxide was discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1043–1051, July, 2007.     

Three-component synthesis of 6-aryl-4-methyl-2-oxo-1,2,3,6-tetrahydropyrimidine-5-(N-aryl)carboxamides

A three-component synthesis using acetoacetanilides and a mixture of an aromatic aldehyde and urea yields 6-aryl-4-methyl-2-oxo-1,2,3,6-tetrahydropyrimidine-5-(N-aryl)carboxamides.     

Synthesis,structural and theoretical investigations on 3-diethyl 2-({4-[3-ethoxy-2-(ethoxycarbonyl)-3-oxo-2-phenylpropyl]-2,5-dimethylphenyl}methyl)-2-phenylpropanedioate

Because bioactive ester derivatives are important pharmacophores, the current study focuses on the synthesis and evaluation of their pharmacological activity. In this case, novel 1,3-diethyl 2-(4-[3-ethoxy-2-(ethoxycarbonyl)-3-oxo-2-phenylpropyl]-2,5-dimethylphenylmethyl)-2-phenylpropanedioate (C₃₆H₄₂O₈) was synthesized in good yield. Elemental analysis, mass spectroscopy, FT-IR and NMR spectroscopy are used to analyse the compound. The X-ray diffraction examination of a single crystal indicates that the molecular structure crystallises in the monoclinic space group P21/n, with half of the molecule being crystallographically unique (Z' = 0.5) with Z = 2. Surprisingly, the inversion centre is located at the centre of the methyl-substituted benzene ring, which generates the entire molecule via symmetry operation. Crystallographic and computational chemistry technologies are used to examine the nature and strength of intermolecular interactions amongst inversion-related dimers (Hirshfeld surface, energy framework, QTAIM and NCI analysis). Koopman's approximation was used to calculate the frontier molecular orbitals, HOMO-LUMO energy gap, and associated reactive parameters. Furthermore, molecular docking experiments demonstrated the compound with Antieczematic proteins as well as protein-ligand interactions, hydrogen bond interactions are delibrated.     

Synthesis of substituted N-(2,4-dioxo-1,2,3,4-tetrahydroquinazolinyl)benzamides and N-(2-thiono-4-oxo-1,2,3,4-tetrahydroquinazolinyl)benzamides

Substituted N-(2,4-Dioxo-1,2,3,4-tetrahydroquinazolinyl)benzamides ( 3a-g ) and substituted N-(2-Thiono-4-oxo-1,2,3,4-tetrahydroquinazolinyl)benzamides ( 4a-g ) were synthesized in one step from the reaction of methyl anthranilate with 2-aryl-1,3,4-oxadiazolin-5-ones ( 1a-g ) and 2-aryl-1,3,4-oxadiazoline-5-thiones ( 2a-g ), respectively, in m-cresol at 150–160°. Alternative routes leading to the formation of 3a and 4a are also reported.     

Synthesis and Crystal Structure of Ethyl 4-(3,4-Methylenedioxylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate under Microwave Irradiation

<正>The crystal structure of the title compound (C16H17NO5) has been determined by single-crystal X-ray diffraction. The crystal is of monoclinic, space group C2/c with a = 18.520(2), b = 7.8910(1), c = 21.728(3) A, β = 104.77(1)°, V= 3070.4(7) A3, Mr= 303.31, Z = 8, Dc= 1.312 g/cm3, λ = 0.71073 A,μ(MoKα) = 0.098 mm-1 and F(000) = 1280. The structure was refined to R = 0.0486 and wR = 0.1287. There exist intermolecular hydrogen bonds in the crystal.     

Synthesis and conversions of 3-(4-amino-5-methyl-4H-1,2,4-triazol-3-ylmethylene)-2-oxo-1,2,3,4-tetrahydroquinoxaline

The reaction of the hydrazone 3a with hydrazine hydrate in DBU/ethanol conveniently gave 3-(4-amino-5-methyl-4H-1,2,4-triazol-3-ylmethylene)-2-oxo-1,2,3,4-tetrahydroquinoxaline 6 . The reactions of 6 with an equimolar and 2-fold molar amount of nitrous acid afforded 3-(α-hydroxyimino-4-amino-5-methyl-4H-1,2,4-triazol-3-ylmethyl)-2-oxo-1,2-dihydroquinoxaline 9 and 3-(α-hydroxyimino-5-methyl-2H-1,2,4-triazol-3-ylmethyl)-2-oxo-1,2-dihydroquinoxaline 10 , respectively, which were converted into the 3-heteroarylisoxazolo[4,5-b]quin-oxalines 13a,b and 11 , respectively. Compound 9 was also cyclized into the 8-quinoxalinyl-1,2,4-triazolo-[3,4-f][1,2,4]triazines 14a,b .     

2-乙氨基-6H-5-(1-苯基-3-甲基/苯基-5-吡唑啉酮-4-基)-1,3,4-噻二嗪的合成和晶体结构

利用1-苯基-3-甲基/苯基-4-氯乙酰基-吡唑啉酮-5(PMCP/DPCP)与4-乙基氨基硫脲(ETSC)发生缩合反应,生成了2个新的双杂环化合物2-乙氨基-6H-5-(1-苯基-3-甲基/苯基-5-吡唑啉酮-4-基)-1,3,4-噻二嗪(PMCP-ETSC/DPCP-ETSC),并对其进行元素分析、红外光谱、核磁共振表征和晶体结构分析.PMCP-ETSC晶体属于单斜晶系,Pm空间群,晶胞参数:a=0.7947(1)nm,b=0.8348(1)nm,c=1.1990(2)nm,β=106.07(1)°,V=0.77269(2)nm3,Z=2,Dc=1.356g/cm3,μ=0.219mm-1,F(000)=332,R=0.0298,wR=0.0704.该化合物通过分子间氢键形成沿c轴无限延伸的一维链状结构.DPCP-ETSC晶体属于正交晶系,Pna21空间群,晶胞参数:a=1.1478(2)nm,b=1.3545(2)nm,c=1.1994(2)nm,V=1.8646(4)nm3,Z=4,Dc=1.345g/cm3,μ=0.194mm-1,F(000)=792,R=0.0345,wR=0.0694,此化合物通过分子间氢键形成沿c轴成链状,沿ab平面成波浪状的超分子结构.     

Synthesis,characterization, crystal and molecular structure analysis of a novel 1-benzhydryl piperazine derivative: 1-benzhydryl-4-(2-nitro-benzenesulfonyl)-piperazine

A novel 1-benzhydryl piperazine derivative 1-benzhydryl-4-(2-nitro-benzenesulfonyl)-piperazine was synthesized by the nucleophilic substitution of 1-benzhydryl piperazine with 2-nitro-benzenesulfonyl chloride. The product obtained was characterized spectroscopically and finally confirmed by X-ray diffraction study. The title compound, C₂₃H₂₃N₃O₄S crystallizes in the monoclinic space group C2/c with cell parameters a = 13.1120(9) Å, b = 21.4990(9) Å, c = 16.655(1) Å, β = 111.352(2)°, Z = 8, and V = 4372.7(4) Å. The structure reveals that the piperazine ring is in a chair conformation. The geometry around the S atom is distorted tetrahedral. There is a large discrepancy in the bond angles around the piperazine N atoms. The structure is stablized by C–H···O type intermolecular hydrogen bonding interactions.     

2-methylpyridinium 5-(2,4-dinitrophenyl)-6-oxo-2-thioxo-1,2,3,6-tetrahydropyrimidin-4-olate: Synthesis,crystal structure,and biological evaluation

The titled complex is synthesized from the ethanolic solutions of 1-chloro-2,4-dinitrobenzene, 2-thiobarbituric acid, and 2-methylpyridine and characterized by spectral and elemental analyses. The single crystal X-ray diffraction results for the complex are compatible with the spectral observations. The titled complex exhibits anticonvulsant activity and reduces all phases of convulsion even at a low dosage. Acute toxicity studies of the complex are performed to understand the safer dose concentration for clinical trials.     

Synthesis, X-ray diffraction analysis and NMR studies of (Z)-2-methyl-3-triphenylstannyl-3-pentene-2-ol

The synthesis of (Z)-2-methyl-3-triphenylstannyl-3-pentene-2-ol and its characterization by an X-ray diffraction study and multinuclear NMR are reported. The tin atom exhibits a distorted tetrahedral SnC₄ geometry with the four Sn---C bond distances experimentally equivalent. The slight distortion from the ideal tetrahedral geometry is because of the presence of a weak intramolecular HO → Sn interaction of 3.012(3) Å which produces a loose four-membered ring. The title compound was characterized in solution by ¹H, ¹³C and ¹¹⁹Sn NMR, and the persistence of the weak intramolecular HO → Sn coordination in solution was revealed by ¹³C and ¹¹⁹Sn secondary isotope multiplet of partially labelled entities (SIMPLE-NMR) experiments.     

三苯基锡-2-(1, 2-亚乙二硫)亚甲基-3-羰基-5-芳基-4-戊烯酸 酯的合成及晶体 结构

由2-(1,2-亚乙二硫)亚甲基-3-羰基-5-芳基-4-戊烯酸与三苯基氢氧化锡反应,合成了九个标题化合物3。用X射线衍射法测定了3b的晶体结构。该晶体属三斜晶系,空间群P1,a=0.9074(2)nm,b=1.6809(3)nm,c=2.1834(4)nm,α=77.57(3)ⅲ,β=88.04(3)ⅲ,γ=89.47(3)ⅲ,V=3.2503nm^3,Z=2;R=0.0592。由锡氧原子间距离可推测,该晶体中羧酸根作为双齿配体与锡原子形成了分子内五配位结构。     

Multicomponent synthesis and anticancer activity studies of novel 6-(Trifluoromethyl)-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate derivatives

A series of novel 6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives were obtained in good yields from ethyl 4,4,4-trifluoro-3-oxobutanoate, urea, and aryl aldehyde via Biginelli multicomponent reaction. All the corresponding products 4a–4p were examined against four human cancer cell lines (A549, HepG2, COLO205 and DU145) and compounds 4e, 4i, and 4?m which showed promising anticancer activity have been identified.     

Synthesis and alkylation ofN-methylmorpholinium 5-cyano-4-(3- and 4-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates

The reactions of 3- or 4-hydroxybenzaldehydes with cyanothioacetamide and Meldrum's acid in the presence ofN-methylmorpholine affordedN-methylmorpholinium 5-cyano-4-(3-or 4-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates, respectively. The resulting compounds were used in the synthesis of substituted 6-alkylthio-1,2,3,4-tetrahydropyridin-2-ones. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2333–2336. December, 1999.