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1.
A convenient method for the copper(I)-catalyzed arylation of substituted imidazo[1,2-a]pyridine has been developed. This method is applicable to a variety of aryl electrophiles, including bromides, iodides, and triflates. It represents the first general process for C-3 arylation of substituted imidazo[1,2-a]pyridine by Cu(I) catalysis to construct various functionalized imidazo[1,2-a]pyridine core π-systems. 相似文献
2.
Kamal A Devaiah V Reddy KL Rajendar Shetti RV Shankaraiah N 《Journal of combinatorial chemistry》2007,9(2):267-274
A versatile method for the solid-phase synthesis of imidazo[1,2-a]pyridine-based derivatives, imidazo[1,2-a]pyridine-8-carboxamides, has been developed. They were obtained by treatment of the amino group of the polymer-bound 2-aminonicotinate with different alpha-haloketones, followed by halogenation at the 3-position of the polymer-bound imidazo[1,2-a]pyridine. The derived polymer-bound imidazo[1,2-a]pyridines 5, 6, and 7 were finally cleaved from the solid-support with an excess of primary or secondary amines. The final crude products were purified from excess amines by solid-supported liquid-liquid extraction (SLE). 相似文献
3.
L. M. Potikha A. R. Turelik A. V. Shelepyuk V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2012,48(2):343-354
A convenient method is proposed for the preparation of new derivatives of free heterocyclic bases of imidazo[1,2-a]pyridine, pyrido[1,2-a]benzimidazole, and [1,2,4]triazolo[4,3-a]pyridine series. This method entails the dealkylation of N-(2-cyanoethyl)- or N-benzylazolopyridinium quaternary salts in the presence of bases and reaction with ammonium formate in the presence of Pd/C, respectively. 相似文献
4.
The one-pot reaction of β-lactam carbenes with 2-pyridyl isonitriles followed by an acidic hydrolysis was reported, which produced 2-carbonyl-3-(pyridylamino)imidazo[1,2-a]pyridines in moderate to good yields. Among the resulting novel imidazo[1,2-a]pyridine derivatives, 1-(6-chloro-3-(5-chloropyridin-2-ylamino)imidazo[1,2-a]pyridin-2-yl)-2-ethylbutan-1-one was demonstrated to be an efficient fluorescent probe for mercury ion both in acetonitrile and in buffered aqueous solution. 相似文献
5.
R. I. Yurchenko A. D. Ponomarenko N. S. Savina A. A. Tolmachev 《Chemistry of Heterocyclic Compounds》2004,40(12):1543-1545
In reaction with equimolar amount or twice the amount of N-bromosuccinimide 2-(1-adamantyl)-7-methylimidazo[1,2-a]pyridine, obtained from 2-amino-4-methylpyridine and bromomethyl 1-adamantyl ketone, is converted into 2-(1-adamantyl)-3-bromo-7-methylimidazo[1,2-a]pyridine. With three times the amount of N-bromosuccinimide it gives 2-(1-adamantyl)-3-bromo-7-formylimidazo[1,2-a]pyridine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1791–1793, December, 2004. 相似文献
6.
The addition of 2-phenylimidazo[1,2-a]pyridine to a nitrating mixture forms 3-nitro-2-(p-nitrophenyl)imidazo[1,2-a]pyridine; the position of the nitro groups in it has been shown by chemical reactions and by a determination of the dipole moment. 相似文献
7.
[formula: see text] The preparation of the first library of imidazo[1,2-a]pyridine derivatives on a solid support is described. A sulfone linker strategy was applied in the synthesis. Key steps involved in the solid-phase synthetic procedure include (i) alpha-haloketone resin formation by sulfinate-->sulfone alkylation, (ii) imidazo[1,2-a]pyridine ring formation by treatment with 2-aminopyridine, (iii) sulfone anion alkylation, and (iv) traceless product release by oxidation-elimination. A library of 12 imidazo[1,2-a]pyridines was synthesized. 相似文献
8.
The fused heterocyclic compounds 2 : imidazo [1,2-a] pyridine 2a-c and pyrido [1,2-a] pyrimidine 2d were obtained from the reaction of a -cinnamoyl ketene dibenzylthio acetals 1 with diamine. When a -cinnamoyl -a '-benzoyl ketene N, N-acetals 3a-b were treated by t-BuONa/t-BuOH solution, 8- benzoyl-pyrido[1,2-a] pyrimidine 4 was produced. 相似文献
9.
Stable 3-acetyl derivatives of imidazo[1,2-a]benzimidazole were synthesized by the action of acetic anhydride on 2,9-disubstituted imidazo[1,2-a]benzimidazole. The former were also obtained by cyclization of 1-alkyl (aralkyl) -3-acylmethyl-2-iminobenzimidazoline hydrobromides in acetic anhydride in the presence of anhydrous sodium acetate. 3-Benzoyl-substituted imidazo[1,2-a]benzimidazoles, which are unstable in acidic media, were synthesized by the action of benzoyl chloride in the presence of pyridine or excess starting imidazo [1,2-a] benzimidazole.See [1] for communication XI.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 121– 125, January, 1976. 相似文献
10.
M Yamanaka K Miyake S Suda H Ohhara T Ogawa 《Chemical & pharmaceutical bulletin》1991,39(6):1556-1567
A series of 1,2-dihydro-5-imidazo[1,2-a]pyridinyl-2(1H)-pyridonones was synthesized and evaluated for positive inotropic activity, 1,2-Dihydro-5-imidazo[1,2-a]pyridin-6-yl-6-methyl-2- oxo-3-pyridinecarbonitrile (11a) hydrochloride monohydrate (E-1020) was found to be a potent and selective inhibitor of phosphodiesterase III and a long-acting, potent, orally active positive inotropic agent. Additional imidazo[1,2-a]pyridin-2-yl (3a), -3-yl (16), -7-yl (20) and -8-yl (24a) compounds were also prepared. Altering the pyridine substitution from the 2-position to the 6-position produced a 2-fold increase in the i.v. cardiotonic potency (ED50) from 52 to 23 micrograms/kg, while substitution at the 3-, 7- or 8-position reduced potency. In the 2-positional isomers, introduction of halogen groups enhanced the activity and 3-chloro-1,2-dihydro-5-(6-fluoroimidazo[1,2-a] pyridin-2-yl)-6-methyl-2(1H)-pyridinone (3u) was the most potent (i.v. ED50 11 micrograms/kg) in this series. E-1020 is presently under development for the treatment of congestive heart failure. 相似文献
11.
12.
V. A. Anisimova N. I. Avdyunina A. F. Pozharskii A. M. Simonov L. N. Talanova 《Chemistry of Heterocyclic Compounds》1980,16(4):409-417
The interaction of condensed nitrogen-containing bridge systems with chloral has been studied and the high sensitivity of the reaction to the -excess of the initial heteroaromatic system has been established. It has been shown that chloral is a convenient formylating agent for systems with a moderate -excess —imidazo[l,2-a]imidazole, 9H-imidazo[1,2-a]benzimidazole, imidazo[1,2-a]pyridine, imidazo[1,2-a]naphtho[2,3-d]imidazole. Heterocycles with a high -excess (indolizine, pyrrolo[1,2-a]benzimidazole) form cyanine dyes under the action of chloral. Systems with a lowered -excess (1H-imidazo[1,2-a]benzimidazole, imidazo[1,2-a]quinoline, imidazo[2,1-a]isoquinoline, imidazo[1,2-a]perimidine, imidazo[5,1-b]benzoxazole, imidazo[1,2-a]benzothiazole, and imidazo[1,2-a]pyrimidine) do not react with chloral in a neutral medium. However, in a number of cases their foraylation can be carried out in an acid medium.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 528–537, April, 1980. 相似文献
13.
R. Saddik M. Khoutoul N. Benchat B. Hammouti S. El Kadiri R. Touzani 《Research on Chemical Intermediates》2012,38(9):2457-2470
A series of heterocyclic compounds possessing imidazolo[1,2-a]pyridine moiety, namely, ethyl 7-methylimidazolo[1,2-a] pyridine-2-carboxylate L1; 2-(3-nitrophenyl)imidazo[1,2-a]pyridine L2; 3-(imidazo[1,2-a]pyridine-2-yl)aniline L3; 2-phenylimidazolo[1,2-a]pyridine-3carbaldehyde L4; and 2-phenylimidazo[1,2-a]pyridine L5 were synthesized. The in situ generated copper (II), iron (II), and zinc (II) complexes of these compounds (L1–L5) were examined for their catalytic activities and were found to be effective catalysts for the oxidation of catechol to o-quinone with the atmospheric oxygen. The present study reveals that the rate of oxidation depends on four parameters: the nature of the ligand, transition metals, ion salts, and the concentration of the complex. The combination L2(Cu(CH 3 COO) 2 ) gives the highest rate. 相似文献
14.
Pyrazolo[1,5-a]pyridines and 6-iodopyrazolo[1,5-a]pyridines were synthesized by gold-catalyzed and iodine-mediated cyclization of enynylpyrazoles in good to excellent yields, respectively. The iodinated adducts were further converted to 6-arylpyrazolo[1,5-a]pyridines via Suzuki-Miyaura coupling reaction and 6-cyanopyrazolo[1,5-a]pyridine by Ullmann condensation reaction. One of the cyclization adducts, 2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine, was converted to a p38 kinase inhibitor, 2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridine, in two steps. 相似文献
15.
Richard J. Sundberg D. J. Dahlhausen G. Manikumar B. Mavunkel Atanu Biswas V. Srinivasan Fred King Philip Waid 《Journal of heterocyclic chemistry》1988,25(1):129-137
A series of substituted 2-aryl imidazo[1,2-a]pyridines has been prepared in which a variety of substituents are introduced on the 4′-position of the phenyl ring and on the 3, 5 , 6 or 7 position of the heterocyclic ring. Most examples have acetamido, bromo, cyano, or formyl substituents at the 4′-position. Analogous imidazo-[2,1-b]fhiazoles and imidazo[1,2-a]pyrimidines have also been prepared. Another series of compounds consisting of 4′-formylphenoxymethyl derivatives of imidazole, the three positional isomers of pyridine, thiazole, benzimidazole and ring-substituted imidazo[1,2-a]pyridines has been prepared. 2-(4′-Formylphenylethenyl) derivatives of imidazole and imidazo[1,2-a]pyridine were also prepared. 相似文献
16.
Hossaini Z Rostami-Charati F Firoziyan S Sabbaghan M Khalilzadeh MA 《Combinatorial chemistry & high throughput screening》2012,15(6):503-508
An efficient synthesis of dialkyl pyrrolo[2,1-a]isoquinoline-2,3-dicarboxylates, pyrrolo[1,2-a]quinoline-1,2- dicarboxylates and indolizines is described via one-pot reactions of isoquinoline, quinoline or pyridine and phenacyl bromids with dialkyl acetylenedicarboxylates or diaryloylacetylene under solvent-free conditions at 50°C. The mild reaction conditions and high yields of the products exhibit the good synthetic advantage of these methods. 相似文献
17.
The reaction of esters of 3-phenyl-3-chloro-2-oxopropionic acid with 2-aminopyridines and 2-aminoquinoline in chloroform at reflux gave derivatives of imidazo[1,2-a]pyridine and imidazo[1,2-a]quinoline in high yield.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2627–2629, November, 1990. 相似文献
18.
咪唑并吡啶类化合物的合成及其应用* 总被引:2,自引:0,他引:2
咪唑并吡啶类化合物具有与吲哚、氮杂吲哚等类似的特殊结构和良好的生物活性,在医药和农药工业有着广泛的应用,成为有机化学家和药物化学家的研究热点。咪唑并吡啶类化合物主要有咪唑并[4,5-b]吡啶、咪唑并[4,5-c]吡啶、咪唑并[1,2-a]吡啶和咪唑并[1,5-a]吡啶等4个类型。本文阐述了近年来咪唑并吡啶类化合物的合成研究进展和应用情况,主要介绍了咪唑并[4,5-b]吡啶和咪唑并[4,5-c]吡啶这两类化合物的合成方法和在医药及农药领域的应用。 相似文献
19.
M. O. Lozinskii A. F. Shivanyuk P. S. Pel'kis 《Chemistry of Heterocyclic Compounds》1971,7(4):439-442
The exchange and cyclization of phenyliminooxalyl chloride with ammonium thiocyanate, sodium azide, aniline, amidoximes, and diphenylthiourea, and with 2-aminopyridine, 2-aminobenzothiazole, and 2-amino- and 2-mercaptobenzimidazole were studied. The cyclization products are derivatives of thiazolidine, imidazo[1,2-a]pyridine, imidazo[2,1-b]benzothiazole, imidazo[1,2-a]benzimidazole, and thiazolo[3,2-a]benzimidazole. A trimer of 1-phenyltetrazole-5-carboxylic acid was obtained when an attempt was made to convert its azide to the corresponding isocyanate.See [1] for communication II.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 471–474, April, 1971. 相似文献
20.
F. M. A. El-Taweel 《Phosphorus, sulfur, and silicon and the related elements》2013,188(7):1267-1277
Several new thiophene, thiazole, 2H-pyran-2-one, benzimidazo[1,2-a]pyridine and pyridine derivatives were synthesised from active methylene reagents, 4-chloroacetylantipyrine and enaminones as starting materials. 相似文献