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1.
3-Cyclohex-2-enyl-4-hydroxy-1-methylquinolin-2(1H)-one (5) reacts with pyridine hydrotribromide in CH2Cl2 at 0–5°C for 0.75h to give a furo fused heterocycle 6 in 96% yield. Product 6 on treatment with KOH-EtOH eliminates HBr to give compound 8 which on treatement with Pd-C in refluxing diphenyl ether for 0.5h furnishes benzofuro[3,2-c]quinolone 9 in 90% yield. Substrate 5 on sequential treatment with Ac2O-AcONa and Br2/AcOH followed by KOH-EtOH, however produces bicyclic product 7 in excllent overall yield. Substrate 5 reacts with 1 equivalent of m-chloroperbenzoic acid in refluxing benzene to furnish bicyclic heterocycle 12 in 80% yield and with cold conc. H2SO4 at 0–5°C for 2h generates the bicyclic heterocycle 14 in 90% yield. 相似文献
2.
A series of new tetraazaspiro[5,5]-undec-4-ene-2,7,9,11-tetraones have been obtained by reaction of 5-(2-arylethylidene-2-oxo)-1,3-dimethylpyrimidine-2,4,6-triones with ureas. A three-component one-pot procedure to the spiranes synthesis was also developed. One-pot reaction of arylglyoxals, 1,3-dimethylbarbituric acid, and dimethylurea led to imidazolyl-1,3-dimethylbarbituric acids. Mechanisms of studied reactions were discussed. 相似文献
3.
《Journal of Coordination Chemistry》2012,65(11):1337-1351
The reaction of MX2 (M = Co(II), Ni(II); X = Cl, Br) with 2-aminopyrimidine in aqueous acid yields compounds [(2-apmH)2MX4], (2-apmH)2[MX4], or (2-apmH2) [MX2(H2O)4]X2 (2-apmH = 2-aminopyrimidinium; 2-apmH2 = 2-aminopyrimidinium(2+)). All compounds have been characterized by single crystal X-ray diffraction. The compounds [(2-apmH)2MX4] with M = Co, X = Cl (1); M = Ni, X = Cl (3); and M = Ni, X = Br (4) are isomorphous and crystallize as nearly square planar MX4 units with the 2-apmH cations coordinated in the axial sites through the unprotonated ring nitrogen. (2-ApmH)2[CoBr4] (2) crystallizes as the salt with a nearly tetrahedral CuBr4 2- anion. (2-ApmH2)[NiBr2(H2O)4]Br2 (5) forms as a cocrystal of the neutral, six-coordinate nickel complex and (2-ampH2)Br2, stabilized by extensive hydrogen bonding. Crystal data (1): monoclinic, P21/c, a = 7.540(4), b = 12.954(4), c = 7.277(3) Å, β = 110.09(6), V = 667.4(5) Å3, Z = 2, Dcalc = 1.955 Mg/m3, μ = 2.079 mm-1, R = 0.0501 for [|I|≥2(I)]. For (2): triclinic, P-1, a = 7.720(2), b = 7.916(2), c = 14.797(3) Å, α = 97.264(3), β = 104.788(3), γ = 105.171(3)°, V = 825.3(3) Å3, Z = 2, Dcalc = 2.296 Mg/m3, μ = 10.715 mm-1, R = 0.0308 for [|I|≥2(I)]. For (3): monoclinic, P21/c, a = 7.595(3), b = 12.891(4), c = 7.204(3) Å, β = 111.07(3)°, V = 658.2 Å3, Z = 2, Dcalc = 1.982 Mg/m3, μ = 2.279 mm-1, R = 0.0552 for [|I|≥2(I)]. For (4): monoclinic, P21/c, a = 7.840(2), b = 13.358(4), c = 7.518(2) Å, β = 110.923(3)°, V = 938.6(3) Å3, Z = 2, Dcalc = 2.577 Mg/m3, μ = 12.18 mm-1, R = 0.0280 for [|I|≥2(I)]. For (5): orthorhombic, Pnma, a = 16.776(6), b = 11.943(4), c = 7.079(3) Å, V = 1418.2(9) Å3, Z = 4, Dcalc = 2.564 Mg/m3, μ = 12.639 mm-1, R = 0.0381 for [|I|≥2σ(I)]. 相似文献
4.
A simple and novel method to the synthesis of 3-fluoro-4-aryl-2-pyridone from a Michael-adduct of fluoronitroacetate and α,β-unsaturated ketone is reported. With (NH4)2CO3 as the N-source and TsOH as the promoted acid, a series of fluorinated-pyridones was obtained with moderate to good yields. 相似文献
5.
Mahesh R. Kulkarni Nitin P. Lad Vijay M. Khedkar Nitin D. Gaikwad 《Journal of heterocyclic chemistry》2021,58(6):1359-1370
With the aim of expanding the scope of SAR on piperlongumine (PL), a naturally occurring anticancer molecule, we have designed a novel hybrid molecule bearing 3,4-dihydroisoquinolin-1(2H)-one and trans-cinnamic acids. The structure, based on hybridization strategy, is used for hybridization of naturally occurring scaffolds. We have synthesized 14 hybrid molecules by coupling 3,4-dihydroisoquinolin-1(2H)-one core with cinnamic acids using the mix anhydride approach. The newly synthesized inhibitors were evaluated for cell viability against breast cancer MCF-7 and cervical cancer HeLa cell lines. Furthermore, the active compounds were screened for their potential in breast cancer MDA-MB-231, cervical cancer C33A cell lines, prostate cancer DU-145, PC-3, and normal VERO cells. From the series, compound 10g was seen to inhibit MCF-7 cell growth significantly with GI50 < 0.1 μM along with growth inhibition in MDA-MB-231 (GI50 = 20 μM) and C33A (GI50 = 3.2 μM). While the inhibitor 10i inhibits MCF-7 breast cancer cell growth GI50 = 3.42 μM along with inhibition of cell growth in MDA-MB-231 (GI50 = 30 μM), HeLa (GI50 = 7.67 μM), C33A (GI50 = 13 μM), DU-145 (GI50 = 6.45 μM), PC-3 (GI50 = 8.68 μM), and VERO (GI50 = 2.93 μM), respectively. Furthermore, molecular docking study demonstrated these compounds could bind tightly to the colchicine domain of tubulin through a network of favorable steric and electrostatic interactions and thus act as a tubulin polymerization inhibitor. 相似文献
6.
Ali Ramazani Abolfazl Momeni-Movahhed Farideh Gouranlou 《Phosphorus, sulfur, and silicon and the related elements》2013,188(4):903-907
Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by 1-hydroxy-2-acetonaphthone leads to vinyltriphenylphosphonium salts, which undergo aromatic electrophilic substitution reaction with conjugate base to produce dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene) butanedioates. Silica gel was found to catalyze conversion of dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene) butanedioates to dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-2-butenedioates in solvent-free conditions at 90°;C in fairly good yields. 相似文献
7.
Anthranilonitrile reacting with formic acid at room temperature for three days gave 64% of 3-(2-cyanophenyl)quinazolin-4(3H)-one. Under similar conditions anthranilic acid. 4-nitroaniline, and 2,5-dichloroaniline were N-formylated in good yields.Institute of Organic Chemistry and Technology, Silesian Technical University, Krzywoustego, 4, 44–100 Gliwice, Poland; e-mail: wojtex@zeus.polsl.gliwice.pl. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 922–924, July, 2000. 相似文献
8.
Olga O. Krasnovskaya Yuri V. Fedorov Vasily M. Gerasimov Dmitry A. Skvortsov Anna A. Moiseeva Andrei V. Mironov Elena K. Beloglazkina Nikolay V. Zyk Alexander G. Majouga 《Arabian Journal of Chemistry》2019,12(6):835-846
A series of 2-aminosubstituted (5Z)-3-phenyl-5-(pyridine-2-ylmethylene)-3,5-dihydro-4H-imidazole-4-ones (L) was prepared by the reaction of the corresponding 2-alkylthio-3,5-dihydro-4H-imidazole-4-ones with morpholine or piperidine in the presence of ytterbium(III) triflate. The resulting ligands were subsequently reacted with CuCl2·2H2O and CoCl2·6H2O to give the corresponding copper(II) and cobalt(II) complexes, respectively. Analysis revealed that the complexes were formed with an LMCl2 (M = Cu, Co)-type composition in all cases. The structures of the three cobalt complexes prepared in this way were determined by X-ray crystallography. The results revealed that the cobalt ions in these complexes were tetrahedrally coordinated to two chloride anions and two nitrogen atoms from the pyridine and imidazole moieties of the ligand. The electrochemical properties of the ligands and their complexes were evaluated by cyclic voltammetry, and the results revealed that the first stage in the reduction of the Co(II) and Cu(II) complexes involved the reversible formation of the corresponding Co(I) and Cu(I) complexes, respectively. The cytotoxicity activities of the organic ligands and their complexes were evaluated against several cancer cell lines, including MCF-7, A549 and HEK293 cells. The copper complexes of the organic ligands bearing a phenyl or allyl moiety at their N(3) position together with a piperidine substituent at the 2-position of their imidazolone ring exhibited the greatest cytotoxicity of all of the compounds tested in the current study. 相似文献
9.
Acylation of 2-methyl-2H-1, 2-benzothiazin-3(4H)-one 1, 1-dioxide 3 with aryl anhydrides in the presence of dimethylaminopyridine occurs regiospecifically to afford 2-methyl-4-arylcarbonyl-2H1, 2-benzothiazin-3(4H)-one 1, 1-dioxides 2a-f . 相似文献
10.
A simple, efficient, and general method has been developed for the diastereoselective synthesis of 2,3-disubstituted dihydrobenzofurans through reactions of 2-hydroxyaryl-α,β-unsaturated ketones with dimethylsulfonium carbonylmethylides. 相似文献
11.
The interaction of the sodium salts of 3-(1-adamantyl)-1-hydroxy-1-propen-3-one and 4-(1-adamantyl)-1-hydroxy-1-buten-3-one with hydroxylamine, hydrazine, and guanidine leads to the synthesis of 5-(1-adamantyl)-5-hydroxy- and 5-(1-adamantylmethyl)-5-hydroxy-2-isoxazolines, 3-(1-adamantyl)- and 3-(1-adamantylmethyl)pyrazoles, 3-(1-adamantyl)-2-phenylpyrazole, and 4-(1-adamantyl)-2-amino- and 4-(1-adamantylmethyl)-2-aminopyrimidines. 相似文献
12.
13.
An efficient and novel methodology for the synthesis of C-(alkynyl)-pseudoglycals from δ-hydroxy-α,β-unsaturated aldehydes has been developed. 相似文献
14.
Madan G. Barthakur 《Tetrahedron letters》2006,47(28):4925-4927
An efficient one-pot synthesis of substituted 4H-thiopyrans has been accomplished from a three-component reaction of α,β-unsaturated ketones, Lawesson’s reagent and alkynes under microwave irradiation. 相似文献
15.
16.
《Arabian Journal of Chemistry》2022,15(1):103497
A series of 6-(morpholinosulfonyl)quinoxalin-2(1H)-one based hydrazone, hydrazine, and pyrazole moieties were designed, synthesized, and evaluated for their in vitro antimicrobial activity. All the synthesized quinoxaline derivatives were characterized by IR, NMR (1H /13C), and EI MS. The results displayed good to moderate antimicrobial potential against six bacterial, and two fungal standard strains. Among the tested derivatives, six quinoxalin-2(1H)-one derivatives 4a, 7, 8a, 11b, 13, and 16 exhibited a significant antibacterial activity with MIC values (0.97–62.5 µg/mL), and MBC values (1.94–88.8 µg/mL) compared with Tetracycline (MICs = 15.62–62.5 µg/mL, and MBCs = 18.74–93.75 µg/mL), and Amphotericin B (MICs = 12.49–88.8 µg/mL, and MFC = 34.62–65.62 µg/mL). In addition, according to CLSI standards, the most active quinoxalin-2(1H)-one derivatives demonstrated bactericidal and fungicidal behavior. Moreover, the most active quinoxaline derivatives showed a considerable antibacterial activity with bactericidal potential against multi-drug resistance bacteria (MDRB) strains with MIC values ranged between (1.95–15.62 µg/mL), and MBC values (3.31–31.25 µg/mL) near to standard Norfloxacin (MIC = 0.78–3.13 µg/mL, and MBC = 1.4–5.32 µg/mL. Further, in vitro S. aureus DNA gyrase inhibition activity were evaluated for the promising derivatives and displayed potency with IC50 values (10.93 ± 1.81–26.18 ± 1.22 µM) compared with Ciprofloxacin (26.31 ± 1.64 µM). Interestingly, these derivatives revealed as good immunomodulatory agents by a percentage ranging between 82.8 ± 0.37 and 142.4 ± 0.98 %. Finally, some in silico ADME, toxicity prediction, and molecular docking simulation were performed and showed a promising safety profile with good binding mode. 相似文献
17.
A series of novel 2-hydrazinylpyrido[2,3-b]pyrazin-3(4H)-one derivatives were synthesized and evaluated for their cytotoxic activities against A549,MDA-MB-231 and HT-29 cell lines in vitro.Pharmacological data indicated that compounds 5b,5c,10a and 10g possessed marked cytotoxicity,especially 10a(with IC50 values of 0.81,2.56 and 1.63μmol/L against A549,MDA-MB- 23 1 and HT29 cell lines,respectively),which had emerged as a lead compound. 相似文献
18.
By reacting 1-acetyl- or 1-ethoxycarbonylehloromethylene-2-arylhydrazines ( 2a-c ) with anthranilic acids (1a-b) the corresponding C-acetyl- or C-ethoxyearbonylcarbohydrazonamide derivatives (3a-d) were obtained. Ring closure of the carbohydrazonamides with acetic anhydride afforded 2-carboethoxy- or 2-acetyl-3-arylamino-4(3H)quinazolinones ( 4a-d ). The ester derivatives undergo basic hydrolysis with decarboxylation to 3-arylamino-4(3H)quinazolinones ( 5a-b ). 相似文献
19.
LV Zhi-Liang WANG Tian-Tian ZHANG Yi-Kai FENG Ji-Lu SUN Hai-Ling LIU Jia LIKe 《结构化学》2009,28(12):1640-1644
The title compound (Z)-1-(3-fluorobenzyl)-5-((3-fluorobenzylimino)(2-hydroxy-4- methoxyphenyl)methyl)pyridin-2(1H)-one (C27H22F2N2O3,Mr = 460.47) was synthesized and crystallized. The crystal belongs to the triclinic system,space group P1 with a = 9.951(6),b = 10.059(6),c = 12.927(7)A,α = 109.828(7),β = 102.304(7),γ = 104.898(7)°,Z = 2,V = 1110.2(11)A^3,Dc =1.377 Mg/m^3,μ(MoKα) = 0.102 mm^-1,F(000) = 480,the final R = 0.0449 and Rw = 0.1250 for 4595 observed reflections (I 〉 2σ(I)). X-ray analysis reveals that both m-fluorobenzyl groups are diorientationally disordered because of the rotation of C–C single bond which was represented as F(1),F(2) and F(1'),F(2'). The diorientational disorder was refined and gave the occupancies of 0.665(4) and 0.335(4) for F(1) and F(1'),0.631(3) and 0.369(3) for F(2) and F(2'). Hydrogen bonds existing in the cell link different components to stabilize the crystal structure. The active data proved that the title compound has good anti-HBV activity. 相似文献
20.
V. A. Dorokhov O. G. Azarevich V. S. Bogdanov L. S. Vasil'ev 《Russian Chemical Bulletin》1997,46(1):122-125
Two approaches to the use of 3-acetyl-2-amino-4-hydroxy-1,3-pentadienecarbonitrile (1) in heterocyclic synthesis are considered.
A method for preparing 3-acetyl-4-amino-5-cyano-2-methylpyridine directly from1 andN,N-dimethylformamide dimethylacetal (DMF DMA) was proposed, together with a synthetic route to 2-(2-amino-3-cyano-6-hydroxy-phenyl)-8-cyano-5-hydroxy-4-methylquinoline
based on the transformation of hydroxyvinyl ketone1 into its diphenylboron chelate and condensation of the latter with DMF DMA.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 127–130, January, 1997. 相似文献