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1.
Krivonogov V. P. Kozlova G. G. Sivkova G. A. Spirikhin L. V. Abdrakhmanov I. B. Murinov Yu. I. Tolstikov G. A. 《Russian Journal of Organic Chemistry》2003,39(2):257-260
A reaction was studied of previously unknown 1,3-bis(2-hydroxy-3-chloropropyl)uracil, 1,3-bis(2- hydroxy-3-chloropropyl)-6-methyluracil, and 1,3-bis(2-hydroxy-3-chloropropyl)-5-fluorouracil with 1,3-bis[3-(3-methyl-2H-5-pyrazolon-1-yl)-2-hydroxypropyl]-6-methyluracil. 相似文献
2.
Cyclization of 1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)carbonyl-4-R-thiosemicarbazides in basic medium gave 6-(4-R-5-thioxo-1,2,4-triazol-3-yl)pyrimidine-2,4-diones
(R = Allyl, Ph). Alkylation of the latter with iodomethane occurred at the sulphur atom to give the corresponding methylsulfanyl
derivatives. Acetylation using acetyl chloride occurred at the N(1) atom of the triazole ring to the corresponding acetyl derivative when R = Ph but for R = Allyl the acetylation did not occur
under the same conditions. In the presence of bromine in refluxing methanol the indicated allyl-substituted compound cyclizes
to 6-bromomethyl-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)-5,6-dihydrothiazolo[2,3-c]-1,2,4-triazole. Under Mannich and
bromination conditions the methylsulfanyl derivatives prepared form derivatives at the 5 position of the uracil ring: 5-methylmorpholino-(piperidino)-and
5-bromo-(4-R-5-thioxo-1,2,4-triazol-3-yl)pyrimidine-2,4-diones respectively.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 906–912, June, 2006. 相似文献
3.
Reaction of 2-[6-methyl-2,4-dioxo-1-(thietan-3-yl)-1,2,3,4-tetrahydropyrimidin-3-yl]acetic acid hydrazide with β-dicarbonyl compounds proceeds regioselectively; the structure of the formed hydrazones is governed by the structure of the β-dicarbonyl reaction component. The reaction with acetyl- and propionylacetone afforded 3-[2-(5-alkyl-3-methyl-1H-pyrazol-1-yl)-2-oxoethyl]-6-methyl-1-(thietan-3-yl)pyrimidin-2,4(1H,3H)-diones, with aroylacetones, 5-hydroxypyrazoline derivatives which are present in DMSO solutions in E′ conformation with respect to the amide bond. The condensation products with acetoacetic acid derivatives have a linear structure and consist of mixtures of E,Z- and E′,Z′-isomers owing to the geometric and conformational isomerism. 相似文献
4.
V. P. Krivonogov G. A. Sivkova Yu. I. Murinov G. G. Kozlova I. B. Abdrakhmanov' L. V. Spirikhin N. G. Afzaletdinova R. A. Khisamutdinov 《Russian Journal of Organic Chemistry》2001,37(12):1786-1790
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. 相似文献
5.
S. P. Gasparyan M. V. Alexanyan G. K. Arutyunyan A. H. Martirosyan R. V. Paronikyan H. M. Stepanyan 《Russian Journal of Organic Chemistry》2016,52(8):1179-1182
In reaction of 6-aminouracyles with ethyl oxochloroacetate ethyl 2-(6-amino-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-2-oxoacetates were obtained, which by further reaction with various amines afforded oxo(pyrimidinyl)acetamides. According to the data of biological tests, the synthesized compounds showed low antibacterial and antitumor activity. 相似文献
6.
A series of 5-substituted-3-[{5-(6-methyl-2-oxo/thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidin-5-yl)-1,3,4-oxadiazol-2-yl}-imino] -1,3-dihydro-2H-indol-2-one were synthesized,characterized and screened for their anti-tubercular and antimalarial activity. 相似文献
7.
Jaroslaw Spychala 《合成通讯》2013,43(14):2497-2506
One-stage preparation of 1-[ω-(1,4,5,6-tetrahydropyrimidin-2-yl)alkyl]-thymines from 1-(ω-cyanoalkyl)thymines and a 1:1-mixture of 1,3-diaminopropane and ethanol saturated with hydrogen sulfide is described. 1-(2-Cyanoethyl)-thymine gave a facile reversal of the Michael reaction to thymine under the conditions used. The reaction of 1,3-bis(3-cyanobenzyl)thymine with the above reagent produced 1,3-bis[3-(1,4,5,6-tetrahydropyrimidin-2-yl)benzyl]thymine. 相似文献
8.
Romualdas Smicius Virginija Jakubkiene Milda M. Burbuliene Povilas Vainilavicius 《Monatshefte für Chemie / Chemical Monthly》2002,7(1):173-181
Treatment of 5-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazole-2-thione with haloalkanes yielded oxadiazole S-alkyl derivatives, whereas its reaction with formaldehyde and amines resulted in formation of oxadiazole N(3)-aminomethyl derivatives. The alkylation of 2-alkylsulfanyl-5-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazoles with methyl bromoacetate proceeded at the N(1)-position of pyrimidine to give 2-alkylsulfanyl-5-(1-methoxycarbonylmethyl-6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazoles, whereas aminomethylation, bromination, or nitration took place at position 5 of pyrimidine ring and afforded the corresponding 5-pyrimidine substituted derivatives. 相似文献
9.
《Mendeleev Communications》2021,31(5):698-700
A new type of four component tandem Knoevenagel–Michael reaction has been found consisting in the assembly of benzaldehydes, N,N'-dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one and morpholine in alcohols, other organic solvents or water at room temperature without catalyst or any other additives, which results in the selective formation of unsymmetrical scaffold with three different heterocyclic rings in 63–98% yields. The crystal structure of morpholinium 5-[(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)(4-nitrophenyl)methyl]-1,3-dimethyl-2,6-dioxo-1,2,3,4-tetrahydropyrimidin-6-olate has been confirmed by X-ray diffraction. 相似文献
10.
Romualdas Smicius Virginija Jakubkiene Milda M. Burbuliene Povilas Vainilavicius 《Monatshefte für Chemie / Chemical Monthly》2002,133(2):173-181
Summary. Treatment of 5-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazole-2-thione with haloalkanes yielded
oxadiazole S-alkyl derivatives, whereas its reaction with formaldehyde and amines resulted in formation of oxadiazole N(3)-aminomethyl
derivatives. The alkylation of 2-alkylsulfanyl-5-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazoles
with methyl bromoacetate proceeded at the N(1)-position of pyrimidine to give 2-alkylsulfanyl-5-(1-methoxycarbonylmethyl-6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazoles,
whereas aminomethylation, bromination, or nitration took place at position 5 of pyrimidine ring and afforded the corresponding
5-pyrimidine substituted derivatives.
Received May 9, 2001. Accepted (revised) August 17, 2001 相似文献
11.
E. S. Krylova V. E. Semenov V. D. Akamsin V. S. Reznik 《Russian Journal of General Chemistry》2010,80(7):1364-1368
By condensation of thiourea with 6-methyluracyl derivatives containing ketone and ketoester fragmenst in the alkyl chains
attached to the nitrogen atoms of the pyrimidine ring the products containing 6-methyl- or 3,6-dimethyluracyl fragment and
one or two 6-methyl-4-oxo-2-thio-1,2,3,4-tetrahydropyrimidin-5-yl fragments were synthesized. These compounds can be alkylated
with alkyl bromides. 相似文献
12.
Povilas Vainilavicius Romualdas Smicius Virginija Jakubkiene Sigitas Tumkevicius 《Monatshefte für Chemie / Chemical Monthly》2001,132(7):825-831
Summary. In the reaction of 5-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazole-2-thione with hydrazine
hydrate, 5-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-4-amino-1,2,4-triazole-3-thione was formed. The reactions
of the latter with ethyl bromoacetate and chloroacetonitrile in the presence of triethylamine proceeded under formation of
the corresponding S-alkylated derivatives, whereas from its reaction with ω-bromoacetophenone and ethyl 4-chloroacetoacetate
triazolothiadiazines were obtained. Treatment of the title compound with ethyl 2-chloroacetoacetate led to the formation of
5-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-4-N-acetylamino-(3-ethoxy-carbonylmethylthio)-1,2,4-triazole.
Performing of the latter reaction without basic catalyst gave a triazolothiadiazine. Treatment of the S-alkylated derivatives
with sodium methoxide resulted in triazolothiadiazines via a cyclocondensation reaction.
Received November 20, 2000. Accepted January 15, 2001 相似文献
13.
A series of 5-substitued-3-(5-(4-(furan-2-yl)-6-methyl-2-oxo/thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1,3,4-thiadiazol-2- ylimino)indolin-2-one derivatives were synthesized,characterized and were screened for anti-bacterial,anti-fungal and antitubercular activity. 相似文献
14.
Fattakhov S. G. Solov'eva S. E. Efremov Yu. Ya. Rizvanov I. Kh. Reznik V. S. 《Russian Journal of General Chemistry》2001,71(3):469-470
Mannich reaction of 1,3-bis[4-(2-mercaptomethylphenoxy)butyl]-6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione, formaldehyde, and N-benzylamine afforded a 24-membered macrocyclic compound containing an uracil fragment, 1,3-(11-benzyl-6,7:15,16-dibenzo-5,17-dioxa-9,13-dithia-11-aza-6,15-heneicosadiene-1,21-diyl)-6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione. 相似文献
15.
Novel tandem hydration of alpha-thiocyanatoketones to thiocarbamates followed by in situ cyclodehydration to fused 2-oxo-3-thiazolines is described. The reaction is applied to the synthesis of [1,3]thiazolo[5,4-c]quinoline-2,4(3aH,5H)-diones (4). Concentrated sulfuric acid was found to be critical for the reaction as both corresponding 2,3-dioxo-1,2,3,4-tetrahydroquinolin-3-yl thiocyanates (2) and S-(2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl) thiocarbamates (3) rapidly hydrolyze in the presence of water to 4-hydroxyquinolin-2(1H)-ones (1). 相似文献
16.
F. Valiyev V. Abbasov H. J. Liu F. Y. Tsai 《Journal of the Iranian Chemical Society》2010,7(3):597-602
Syntheses of dinucleotide analogs, (S,R) cis-(4-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-dioxolan-2-yl)methyl (2R,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl hydrogen phosphate (5a) and (S,R) cis-(5-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-oxathiolan-2-yl)methyl (2R,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl hydrogen phosphate (5b), were accomplished by the use of a new strategy. The use of phenyldichlorophosphate (Method A) as the coupling reagent was shown to possess superiority relative to the reported use of di(1H-benzo[d][1,2,3]triazol-1-yl)phenyl phosphonate (Method B). 相似文献
17.
New Schiff bases of 5-aminouracil have been synthesized by the 1: 1 condensation with N-heterocyclic aldehydes. The new compounds were characterized by elemental analyses and 1H NMR spectroscopy. Under similar conditions, the condensation of 6-aminouracil with aldehydes failed to yield the desired Schiff base. Interestingly, the reaction of 6-aminouracil with 6-methylpyridine-2-carbaldehyde resulted in an unusual compound, 2-methyl-6-[7-(6-methylpyridin-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimido[4,5-d]pyrimidin-5-yl]-pyridinium methanesulfonate, whose crystal structure was elucidated by X-ray crystallography. 相似文献
18.
V. E. Semenov O. A. Lodochnikova A. T. Gubaidullin O. N. Kataeva A. V. Chernova Y. Ya. Efremov S. V. Kharlamov Sh. K. Latypov V. S. Reznik 《Russian Chemical Bulletin》2008,57(1):124-136
Reaction of α,ω-bis(3,6-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)alkanes with paraformaldehyde leads to pyrimidinophanes,
which contain four 3,6-dimethyluracil fragments, connected to each other by the methylene chains. A comparative study of intra-
and intermolecular interactions of “open” and macrocyclic uracil derivatives in the crystal state and in solution was performed.
According to the NMR spectroscopy data, there is no self-association of “open” and macrocyclic compounds in chloroform solutions,
whereas the X-ray data revealed the intermolecular π-π contacts between the 3,6-dimethyluracil fragments in the crystals of
these compounds. Conclusions on the presence of intramolecular interactions in chloroform solutions of α,ω-bis(3,6-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)alkanes
and pyrimidinophanes were made based on the UV spectra, which were interpreted in terms of hypo- and hyperchromic effects
relatively to the model uracil derivative. These conclusions correlate with the X-ray data: there are no intramolecular π-π
contacts between the 3,6-dimethyluracil fragments both in the crystals and in solutions of “open” compounds, positions of
these fragments relatively to each other in the molecules of pyrimidinophanes are defined by the lengths of the polymethylene
bridges. The intramolecular stacking effect between the opposite uracil rings is observed for the macrocycles with trimethylene
and hexamethylene chains, whereas there is no such interactions in pyrimidinophanes with tetramethylene chains.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 119–131, January, 2008. 相似文献
19.
AbstractThe building block synthon, 1-(4-(1,3-diphenyl-1H-pyrazol-4-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethan-1-one was efficiently synthesized by Biginelli reaction of 1,3-diphenyl-1H-pyrazole-4-carbaldehdye, acetylacetone, and thiourea and submitted to react with ethyl chloroacetate and chloroacetyl chloride under different conditions to afford some N-heterocycles integrated with pyrazole scaffold. Hydrazinolysis of the pyrimidinethione was studied under different conditions. The insecticidal activity for these compounds, DFT calculations, and docking were run and discussed. Some of them exhibited 100% mortality against Nilaparvata lugens and Mythimna separata. 相似文献
20.
A general four-step approach to 1,2,3,7,8,8a-hexahydropyrido[4,3-d]pyrimidin-2-ones via Staudinger/intramolecular aza-Wittig reaction of 5-acyl-4-(β-azidoalkyl)-1,2,3,4-tetrahydropyrimidin-2-ones promoted by PPh3 was developed. Synthesis of the starting pyrimidinones included preparation of 3-azidoaldehydes by the addition of hydrazoic acid to α,β-unsaturated aldehydes, transformation of 3-azidoaldehydes into N-[(3-azido-1-tosyl)alkyl]ureas followed by the reaction with enolates of dibenzoylmethane, benzoylacetone, acetylacetone, or ethyl 2,4-dioxo-4-phenylbutanoate and dehydration of the resulting products under acidic conditions. 相似文献