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1.
A new series of 2,3-disubstituted quinoline derivatives were synthesized from 2-chloroquinoline-3-carbaldehyde. In the reaction sequence, acetanilide was cyclized to give 2-chloroquinoline-3-carbaldehyde 1 , which was transformed to 2-(4-phenylpiperazin-1-yl)quinolin-3-carbaldehyde 2 by reaction with 4-phenylpiperazine in DMF-containing anhydrous K2CO3; then, compound 2 was oxidized by iodine in methanol, and methyl 2-(4-phenylpiperazin-1-yl)quinoline-3-carboxylate 3 was synthesized. The key intermediate 4 , 4-amino-5-[2-(4-phenylpiperazin-1-yl)quinolin-3-yl]-4H-1,2,4-triazole-3-thiol, was prepared using the ester 3 by a series of step. Reaction of 5 with various aromatic carboxylic acids or phenacyl bromides yielded 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 5a-c and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines 6a-c , respectively. Moreover, compound 2 condensed with o-phenylenediamine to give 2-[2-(4-phenylpiperazin-1-yl)quinolin-3-yl]-1H-benzimidazole 7 . Interaction of 7 and 2-chloromethyl-5-aryl-1,3,4-oxadiazoles in the presence of K2CO3 led to the title compounds 8a-c . Furthermore, 4,5-dihydroisoxazoline derivatives 9a-c were obtained by the reaction of readily accessible starting materials including 2-(4-phenylpiperazin-1-yl)quinolin-3-carbaldehyde 2 , 1-phenyl-2-(triphenylphosphoranylidene)ethanone and hydroximoyl chlorides under mild conditions in the presence of Et3N. The hydrazone intermediates 10a-c were obtained by the condensation of 2 with aroylhydrazides in ethanol, then, refluxing in acetic anhydride yielded 3-acetyl-5-aryl-2-[2-(4-phenylpiperazin-1-yl)quinolin-3-yl]-2,3-dihydro-1,3,4-oxadiazoles 11a-c . Structures of these compounds were established by their elemental analysis, IR, 1H NMR, and mass spectral data. 相似文献
2.
F. A. Amer M. Hammouda A.-A. S. El-Ahl B. F. Abdel-Wahab 《Chemistry of Heterocyclic Compounds》2007,43(12):1559-1566
New pyrrolo[3,4-c]isoxazole derivatives were synthesized from the key intermediates 4-cyanopyrrolidin-3-ones in two steps.
Pyrrolo[2,3-d][1,2,3]triazoles and triazolo[4,5-c]pyridazine were obtained from 2-arylhydrazono-4-cyano-1-(4′-methoxyphenyl)-3-oxopyrrolidines
by refluxing with phenylhydrazine in either ethanol or glacial acetic acid. Aldol self-condensation of 1-aryl-4-cyanopyrrolidin-3-ones
afforded dipyrrolo-[3,2-b:3′, 4′-d]pyran derivatives.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1841–1848, December, 2007. 相似文献
3.
2-取代-3-芳基-4-噻唑啉(硫)酮衍生物的合成、晶体结构和生物活性 总被引:1,自引:0,他引:1
从2-取代-3-芳基-4-噻唑啉酮(4a~4e和5)合成了三个系列新型噻唑啉酮衍生物, 即5-芳基亚甲基-4-噻唑啉酮(6a~6j), 4-噻唑硫酮(7a~7e和8)和4-氰基亚胺基噻唑烷(11a~11e和12). 中间体4a~4e和5由醛、胺和巯基乙酸缩合得到. 所有化合物的结构均经元素分析和1H NMR确证, 并且采用X射线单晶衍射分析方法测定了化合物4b的结构. 初步生物活性试验结果表明, 部分标题化合物具有一定的杀菌活性和促进黄瓜子叶生根活性. 相似文献
4.
1,4-二氢-4-芳基-3,5-吡啶二羧酸酯的合成及表征 总被引:1,自引:0,他引:1
基于二氢吡啶化合物的构效关系, 设计了一系列1,4-二氢-4-芳基-3,5-吡啶二羧酸酯新化合物. 含有易于水解基团的1,4-二氢-4-芳基-3,5-吡啶二羧酸酯类化合物在碱性条件下水解合成了重要中间体1,4-二氢-4-芳基-3,5-吡啶二羧酸单酯, 收率93%~99.8%. 该二羧酸单酯与α-溴代芳基乙酮在相转移剂催化下反应合成目标化合物, 收率74%~99%. 中间体和目标化合物经1H NMR, 13C NMR, IR, MS和元素分析等确证. 相似文献
5.
A straightforward and highly efficient series of new substituted 3-aryl-1,8-naphthyridine derivatives 3a–e, 4a–e, and 6a–e were synthesized. Condensation dissimilar quantities of 2-chloro-3-aryl-1,8-naphthyridine 1a–e with benzene-1,4-diamine 2 and sodium ethoxide refluxing in ethanol solvent yielded the compounds 3a–e and 4a–e. The 2-(4-((3-aryl-1,8-naphthyridin-2-yl)amino)phenyl)isoindoline-1,3-diones 6a–e were obtained by treatment of compounds 3a–e with phthalic anhydride 5 in refluxing N,N-dimethylformamide is described. All synthesized compounds evaluated for their antimicrobial activity. The structures of the compounds have been proven on the established of spectral (IR, 1H NMR, and 13C NMR) data and elemental analyses. The reaction will be characterized by good efficacy, easy workup, simple purification of the products, and availability of catalyst. 相似文献
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7.
S. P. Bondarenko M. S. Frasinyuk V. P. Khilya 《Chemistry of Heterocyclic Compounds》2010,46(5):529-535
The reaction of the analogs of natural 3-arylbenzopyran-2-ones with electrophilic reagents of aminal structure was studied.
Substituted 8-aminomethyl-3-aryl-7-hydroxycoumarins were synthesized. The optimum conditions were determined for the production
of 9-alkyl- and 9-(het)arylmethyl derivatives of 3-aryl-9,10-dihydro-2H,8H-chromeno[8,7-e][1,3]oxazin-2-one in the series of analogs of natural 3-arylbenzopyran-2-ones. 相似文献
8.
9.
Asma Balakrishna Kalluraya Nagaraja Manju Chigahally Lakshmegowda Sharath 《Journal of heterocyclic chemistry》2020,57(8):3105-3115
A novel series of 5-(p-(prop-2-ynyloxy)phenyl)-3-aryl-4,5-dihydropyrazole-1-carbothioamides 2a-f and functionalized 2-(3-(aryl)-5-(4-(prop-2-ynyloxy)phenyl)-4,5-dihydropyrazol-1-yl)-4-(3-arylsydnone-4-yl)thiazoles 4a-l were synthesized. The newly synthesized compounds were elucidated by analytical and spectral analysis. From the single-crystal X-ray diffraction method, it was observed that 2d crystallizes in a monoclinic crystal system with P21/n space group. The compounds 2d crystallized with cell parameters a = 15.0614 (19) Å, b = 6.0805 (7) Å, c = 20.903 (7) Å, α = 114.136 (6)o, β = 110.709 (14) o, γ = 96.553 (5) o, V = 1790.6 (4) Å3, Z = 4. From the Hirshfeld surface computational method, the major intercontacts present in these molecules are H…H (31.6%), C…H (18.2%) and S…H (12.2%), respectively. The newly synthesized compounds were tested for their ability to bleach 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical using DPPH scavenging assay. Among the synthesized compounds carbothioamide compounds 2c (90.7%) and 2b (89.8%) exhibited good DPPH scavenging activity compared to the rest of the compounds. Most of the synthesized carbothioamide molecules ( 2a-f ) found to be potent compared to the thiazole derivatives ( 4a-l ). 相似文献
10.
D. M. Musatov E. V. Starodubtseva A. K. Rakishev O. V. Turova M. G. Vinogradov 《Russian Journal of Organic Chemistry》2011,47(8):1199-1203
A series of new 3-(aminomethyl)pyrazoles and 3-(aminomethyl)isoxazoles was synthesized along a route involving the formation
as key intermediates of esters of 5-substituted 1H-pyrazole-3-carboxylic and 1H-isoxazole-3-carboxylic acids. All compounds obtained were characterized by physicochemical constants, IR, 1H, 13C NMR, and mass spectra. 相似文献
11.
《Arabian Journal of Chemistry》2014,7(4):436-447
A series of 4-(1-aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzenesulfonamide derivatives (1–20) was synthesized and evaluated for its in vitro antimicrobial and anticancer activities. Antimicrobial results indicated that compounds N-(4-(1-benzoyl-5-chloro-2-oxoindolin-3-ylideneamino) phenylsulfonyl)-4-isopropoxy benzamide (9) and N-(4-(5-chloro-1-(2-chlorobenzoyl)-2-oxoindolin-3-ylideneamino) phenylsulfonyl)-4-isopropoxybenzamide (19) were found to be the most effective ones. The anticancer results indicated that almost all the synthesized compounds were more active than the standard drug carboplatin but less active than the standard drug 5-fluorouracil (5-FU) against both the cell lines (HCT116 and RAW 264.7). 4-(1-Benzoyl-5-chloro-2-oxoindolin-3-ylideneamino)-N-(pyrimidin-2-yl) benzenesulfonamide (3) was found to be most potent and exhibited selectivity toward HCT 116. QSAR studies indicated that antimicrobial activity of isatin derivatives against different microbial strains was governed by lipophilic parameter, log P and topological parameters valance zero and third order molecular connectivity indices (0χv and 3χv). 相似文献
12.
For the first time, 4-trifluoromethylthio-3-pyrazoline-5-thione derivatives 4 were synthesized by the reaction of trifluoromethylsulfenyl chloride with nickel complexes of β-aminothiocinnamic acid anilide 3. Complexes 2 and 3 were obtained from 5-aryl-4-thiocarbamoyl-1H-pyrrole-2,3-dione 1. The structure of products 4 has been elucidated on the basis of the elemental analysis and IR.MS. 1H, 19F, 13C NMR spectra. 相似文献
13.
Prakasam Thirumurugan 《Tetrahedron letters》2009,50(28):4145-3867
A series of 4-aryl-6-(1H-indol-3-yl)-2,2-bipyridine-5-carbonitrile derivatives were synthesized via a one-pot multi-component reaction of aromatic aldehydes, 3-(cyanoacetyl)indole and 2-acetyl pyridine in ammonium acetate by conventional heating and microwave irradiation under solvent-free condition. Also a series of 6,6′-di(1H-indol-3-yl)-4,4′-diaryl-2,2′-bipyridine-5,5′-dicarbonitrile derivatives were synthesized using cinnamils, 3-(cyanoacetyl)indole and ammonium acetate. The methodology affords high yields of product at short reaction time. 相似文献
14.
15.
Xin Ming Zhou Zhi Bing Zheng Hong Ying Liu Wu Zhong Jun Hai Xiao Li Li Wang Song Li 《中国化学快报》2007,18(8):905-908
A new series of compounds,1-aryl-3-(3,4-dihydro-2H-chromen-5-yl) ureas,have been synthesized and their structures were confirmed by FAB-MS and ~1H NMR.The preliminary pharmacological screening showed that these compounds inhibited TNF-αproduction in lipopolysaccharide (LPS)-stimulated THP-1 cells. 相似文献
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17.
Manjunatha Bhat G. K. Nagaraja Reshma Kayarmar S. V. Raghavendra K. P. Rajesh H. Manjunatha 《Research on Chemical Intermediates》2016,42(12):7771-7792
A new series of 2-(3-chloro-2-fluorophenyl)-5-aryl-1,3,4-oxadiazole (3a–j) and 2-(aryl sulfanyl)-5-(3-chloro-2-fluorophenyl)-1,3,4-oxadiazole (5a–e) were synthesized via a multistep reaction from 3-chloro-2-fluoro benzoic acid. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, mass spectral data and elemental analysis. They were also screened for their in vivo anti-convulsant and anti-inflammatory activities. Some of them exhibited significant biological activities and were well supported by in silico molecular docking studies for the inhibition of cyclooxygenase-2 (PDB ID: 1CX2) and voltage-gated sodium channels (PDB ID: 4F4L) comparable with the standard drugs. Thus, they were believed to be good inhibitors of cyclooxygenase-2 (PDB ID: 1CX2) and voltage-gated sodium channels (PDB ID: 4F4L). 相似文献
18.
Jairo Quiroga Mario Alvarado Braulio Insuasty Rodolfo Moreno Enrique Ravia Isabel Estevez Regina H. De Almeida S. 《Journal of heterocyclic chemistry》1999,36(5):1311-1316
This paper describes the synthesis of a new series of 6-amino-4-aryl-5-cyanopyrazolo[3,4-b]pyridines 4 and 4-aryl-5-cyano-6H-pyrazolo[3,4-b]pyridin-6-ones 5 from the reaction of 5-amino-3-methyl-1-phenylpyrazole 1 with arylidene derivatives of malonodinitrile 2 and ethyl cyanoacetate 3 . The structure of the final compounds was determined on the basis of nmr measurements, especially by 1H, 1H-, 1H, 13C-COSY, DEPT and X-ray diffraction. 相似文献
19.
T. V. Beryozkina N. N. Kolos V. D. Orlov R. I. Zubatyuk O. V. Shishkin 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):2153-2162
Interaction of 2-aminothiophenol with β-aroylacrylic acids and their dibromo derivatives led to 2-(2-aryl-2-oxoethyl)-4H-benzo-1,4-thiazin-3-ones. The structure of synthesized compounds was confirmed by IR, 1H, and 13C NMR spectra and X-ray analysis. 相似文献
20.
A series of α-[3-alkyl-3,4-dihydro-2-oxo-2H-1,3-benzoxazin-4-yl]-β-keto ester derivatives 1 (Table I) were synthesized by the condensation of 3-alkyl-3,4-dihydro-4-hydroxy-2H-1,3-benzoxazine-2-ones 3 (2) with β-keto esters 4 in the presence of traces of mineral acids under azeotropic conditions. Condensation of 1 with hydrazines 5 gave pyrazolone derivatives 2 (Table II). Condensation of β-diketone derivatives 6 with hydrazines 5 and with 1,2-benzenediamine ( 8 ) resulted in the formation of pyrazoles ( 7a-c ) and diazepine derivatives 12 (Table III) and 13 , respectively. 相似文献