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1.
N. Z. Tugusheva L. M. Alekseeva A. S. Shashkov V. V. Chernyshev V. G. Granik 《Russian Chemical Bulletin》2006,55(8):1475-1486
New approaches to the synthesis of the previously unknown pyrimidine, 4-amino-2-pyridone, and 4-aminopyridine derivatives
were developed based on the reactions of enaminoamides with dimethylformamide dimethyl acetal. New structural modifications
of 4-amino-2-pyridone derivatives were performed. Numerous compounds of this type, which are of interest for biological studies,
were prepared.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1421–1432, August, 2006. 相似文献
2.
《Tetrahedron》2004,60(23):4983-4987
A series of 6-alkynyl-2,4-diaminopyrimidine derivatives bearing various substituents at alkynyl moiety was prepared by the Sonogashira cross-coupling reaction of 2,4-diamino-6-iodopyrimidine using Pd(PPh3)2Cl2 as catalyst. The same reaction was applied to 2-amino-4,6-dichloropyrimidine. This compound on reaction with 1 equiv. of alkyne gave 6-alkynyl-2-amino-4-chloropyrimidine derivatives as main products, while reaction with three equivalents of alkyne afforded predominantly 4,6-bis-alkynyl-2-aminopyrimidines. Some of the resulting alkynyl pyrimidines showed considerable cytostatic activity. 相似文献
3.
Y. A. Al-Farkh F. H. Al-Hajjar N. R. El-Rayyes H. S. Hamoud 《Journal of heterocyclic chemistry》1978,15(5):759-763
Reactions of acetylenic ketones (Ia-f) with methyl α-naphthylacetate in the presence of sodium methoxide gave the corresponding 6-aryl-3-α-naphthyl-4-phenyl-2-pyrones (IIa-f) which upon refluxing with hydrazine hydrate in ethanol gave the corresponding 1-amino-2-pyridone derivatives (VIa-f). The structure of the products was established by chemical and spectroscopic evidence. 相似文献
4.
N. N. Tonkikh M. V. Petrova A. F. Mishnev K. V. Ryzhanova F. M. Avotin'sh A. Ya. Strakov 《Chemistry of Heterocyclic Compounds》2000,36(7):822-829
The corresponding 2,3-substituted 4(3H)-quinazolinones were obtained in the reactions of 2-methyl- and 2-phenyl-4-oxo-3,1-benzoxazines with 1-amino-1,2,4-triazole, 4-amino-2,3-dimethyl-1-phenyl-5-pyrazolone, 2-amino-5-ethyl-1,3,4-thiadiazole, 3-amino-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydroindazole, 1-amino-3-cyano-4,6-dimethyl-2-pyridone, and 1-amino-3-cyano-6-phenyl-4-trifluoromethyl-2-pyridone. The formation of N-benzolyanthranilamides in the reactions of 2-phenyl-4-oxo-3,1-benzoxazine with 2-amino-5-ethyl-1,3,4-thiadiazole and 1-amino-3-cyano-6-phenyl-4-trifluoromethyl-2-pyridones was exceptional. The structures of two of the products have been confirmed by X-ray crystallography.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 936–943, July, 2000. 相似文献
5.
[reaction: see text] A novel 2-pyridone synthesis via nucleophilic addition of malonic esters to alkynyl imines has been developed. The reaction of dialkylalkyl sodiomalonates with alkynyl imines provided 2-pyridones in good to excellent yields. 相似文献
6.
Yoshinori Tominaga Masanori Kawabe Akira Hosomi 《Journal of heterocyclic chemistry》1987,24(5):1325-1331
Reaction of various active methylene compounds with ketene dithioacetals, bis(methylthio)methylenemalononitrile (1a) and bis(methylthio)methylenecyanoacetamide (1b) gave the corresponding 3-cyano-4-methylthio-2(1H)-pyridone derivatives. The transformation of 4-methylthio-2-oxo-2H-pyran-3-carbonitrile in-to 4-methylthio-2(1H)-pyridone derivatives was also described. 相似文献
7.
Ab initio caculations with RHF/6-31G and MP2/6-31G have been used to study the isomerization of 3-amino-2-pyridone in gas-phase and in water. The results obtained show that 3-amino-2-pyridone is isomerized into 3-amino-2-hydroxy pyridine via a four-center cyclic transition state in the gas-phase, and via a six-center cyclic transition state in water. The activation energies of this reaction are 226.3336(RHF/6-31G) and 171.2269(MP2/6-31G) in gas-phase, and 81.6398(RHF/6-31G) and 59.8668(MP2/6-31G) kJ mol−1 under the condition of a single water molecule as the catalyst, respectively. 相似文献
8.
Malose J. Mphahlele 《Tetrahedron》2010,66(42):8261-8266
Palladium-CuI catalyzed Sonogashira coupling of 2-aryl-4-chloro-3-iodoquinolines with terminal acetylenes (1 equiv) in triethylamine afforded the 2-aryl-3-(alkynyl)-4-chloroquinolines as sole products. The 2-aryl-4-chloro-3-iodoquinolines coupled with excess terminal acetylenes (2.5 equiv) in dioxane/water to yield the 2-aryl-3,4-bis(alkynyl)quinoline derivatives in a one-pot operation. The 2-aryl-3-(alkynyl)-4-chloroquinolines were, in turn, subjected to arylation via Suzuki cross-coupling with arylboronic acid derivatives or amination with methylamine, respectively. The structures of the products of successive Sonogashira and Suzuki cross-couplings were also confirmed by X-ray crystallography. 相似文献
9.
10.
The tautomerism of glutazine and some derivatives is investigated by means of UV- and IR-spectroscopy. It is shown, that two prototrope forms exist, a 4-amino-6-hydroxy-2-pyridone and a 2,6-dioxo-4-amino-1,2,5,6-tetrahydro-pyridien. 相似文献
11.
Maria Teresa Cocco Cenzo Congiu Antonio Maccioni Antonio Plumitallo 《Journal of heterocyclic chemistry》1989,26(6):1859-1862
An efficient route allowing the synthesis of 6-amino and 6-ethoxy-2(1H)-pyridone derivatives by reaction of ethyl cyanoacetimidate, ethyl ethoxycarbonylacetimidate and related acetamidines with diethyl ethoxymeth-ylenemalonate (EMME) is reported. The formation of dienamino derivatives as intermediates and their heterocyclization to the 2(1H)-pyridone derivatives is described. 相似文献
12.
A number of meso-ionic compounds derivatives of the bicyclic system 1,3,4-oxadiazolo[3,2-a]pyridine have been prepared from 1-amino-4,6-diphenyl-2-pyridone, either by thermal way or iminophosphorane () 相似文献
13.
Malononitrile reacted with the title compound to give 6-amino-5-cyano-2-(3,3-dicyano-2-methylallylidene-4-methyl-2H-pyran (3). Treatment of 3 with hot 80% sulfuric acid yielded 4,7-dimethyl-56-hydroxy-2(1H)quinolone. With concentrated aqueous sodium hydroxide, 3 gave 5-amino-3,6-dicyano-4,7-dimethyl-2(1H)quinolone and 5-amino-6-carbamoyl-3-cyano-4,7-dimethyl-2(1H)quinolone. The reaction of 3 with hydrochloric in acetic acid gave a mixture of 6-amino-3,7-dicyano-2,8-dimethyl-4-quinolizone and 3-cyano-4-methyl-6-(3,3-dicyano-2-methylallyl)-2-pyrone. Compound 3 also reacted with methylamine, butylamine and piperidine to give 8-amino-5-cyano-4-methyl-2-pyridone, 6-bulylamino-5-cyano-4-methyl-2-pyridone and 5-eyano-4-methyl-6-piperidino-2-pyridone respectively. 相似文献
14.
Chen L Liu X Xu B Sun C Tao P 《Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy》2011,79(5):1926-1930
3-Cyano-4,6-dimethyl-2-pyridone and 3-cyano-4-methyl-6-phenyl-2-pyridone were synthesized effectively by the reaction of readily available 1,3-diketone and malononitrile directly and in good yield. Upon photoexcitation, 3-cyano-4-methyl-6-phenyl-2-pyridone in ethanol shows strong blue emission. The ground- and excited-state geometries, charge distributions, and excitation energies of 2-pyridone derivatives were evaluated by ab initio calculations. Organic light-emitting diodes (OLED) made using 3-cyano-4-methyl-6-phenyl-2-pyridone as dopant showed blue light emission with a maximum electroluminescence (EL) emission at around 456 nm. 相似文献
15.
The focus of our review is on the methods of synthesis and chemical reactivity of 2-pyridone and some derivatives as 2-chloro-3-nicotinonitrile in addition to the biological activity of the 2-pyridone moiety. 相似文献
16.
Jing Li Hong-Ru Tan Yu-Long An Zhi-Yu Shao Sheng-Yin Zhao 《Journal of heterocyclic chemistry》2020,57(1):486-496
An efficient method for synthesis and demethylation of 3-cyano-4-methoxy-2-pyridone derivatives has been developed. DABCO-induced demethylation can lead to 3-cyano-4-hydroxy-2-pyridones in DMF at 90°C with high yield. The protocol is applicable for the synthesis of 3-cyano-4-hydroxy-2-pyridone derivatives. The method is simple, efficient, and practical. 相似文献
17.
Karl Gewald Margit Gruner Ute Hain Gabriele Süptitz 《Monatshefte für Chemie / Chemical Monthly》1988,119(8-9):985-992
Whereas treatment of the ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate (1) with potassium hydroxide yields the 2-hydroxy-thiophene-3-carbonitrile4 its hydrazone2 is converted into the 1-amino-5-mercapto-2-pyridone derivative6. The transformation of the 2-amino-5-phenylazo-thiophene derivative9 by potassium hydroxide yields the substituted 3-mercapto-pyridazin-6(1H)one10, with sodium ethoxide the 5-phenylhydrazono-2-oxo-thiolen-3-carbonitrile11 is formed. From6 the 5-mercapto-2-pyridone derivatives7 d,e can be obtained. 相似文献
18.
Mehiaoui Nawel Kibou Zahira Gallavardin Thibault Leleu Stéphane Franck Xavier Mendes Ricardo F. Paz Filipe A. Almeida Silva Artur M. S. Choukchou-Braham Noureddine 《Research on Chemical Intermediates》2021,47(4):1331-1348
Research on Chemical Intermediates - Novel substituted bis-(3-cyano-2-pyridone) derivatives were prepared via a powerful method using enaminonitriles push–pull dienes as key building blocks.... 相似文献
19.
P. Molina A. Ferao P. M. Fresneda A. Lorenzo A. Trraga 《Journal of heterocyclic chemistry》1983,20(2):381-384
A convenient synthesis of derivatives of the 4H-pyrido [2,1-b]-1,3,4-oxadiazine ring system from readily available 1-amino-4,6-diphenyl-2-pyridone and phenacyl bromides or arylmethyl ketones is described. 相似文献
20.
《Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy》1994,50(6):1121-1139
The complete assignment of the vibrational spectra of 2(1H)-pyridinone (2-pyridone), 1-D-2(1H)-pyridinone (2-pyridone ND) and 1-methyl-2(1H)-pyridinone (N-methyl-2-pyridone) is obtained from a comparative analysis of their IR and Raman spectra (condensed phase and molar solutions in CHCl3 or CDCl3). For the 2-pyridone centrosymmetrical dimer, the strength of the NH…O hydrogen bond association is discussed. Comparison is made with the recent work of Medhi and of Nowak et al. 相似文献