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1.
A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl)quinolines from Morita-Baylis-Hillman adducts via conjugate addition of thiols followed by reductive cyclization with Fe/AcOH was developed. The 2-methyl-3-(phenylthiomethyl)quinolines were transformed into 2-methyl-3-(phenylsulfonylmethyl)quinolines via m-CPBA-mediated oxidation. 相似文献
2.
A simple and efficient synthesis of pyrazolo[3,4-b] quinolines is described. The synthesis involves reaction of 2-amino-3-cyanoquinoline-4-carboxylates(1) with hydrazine hydrate to give regioselectively only pyrazolo[3,4-b]quinolines (2). No formation of pyridazino quinolines (3) is observed. 相似文献
3.
The action of dimethylformamide in phosphorus oxychloride on acylanilides gives 2-chloro-3-substituted quinolines, which may be dechlorinated to give 3-substituted quinolines in good yield. Similarly, N-nitrosodimethylamine in phosphorus oxychloride converts acylanilides into 2-chloro-3-substituted quinoxazolines. 相似文献
4.
N. G. Kozlov L. S. Yakubovich V. L. Murashko 《Russian Journal of Electrochemistry》2000,36(6):777-780
The condensation of ethyl cyclopentanone-2-carboxylate withN-arylmethylene-2-naphthylamines depending on the conditions of reaction affords 4-aryl-l-ethoxycarbonyl-lH-2,3,4,5-tetrahydrocyclopenta-[c]benzo[f]quinolines, 4-aryl-l-ethoxycarbonyl-lH-2,3-dihydrocyclopenta[c]benzo[f]quinolines, and 4-aryllH-2,3-dihydrocyclopenta[c]benzo[f]quinolines. 相似文献
5.
Mahata PK Venkatesh C Syam Kumar UK Ila H Junjappa H 《The Journal of organic chemistry》2003,68(10):3966-3975
A simple, highly efficient, and regioselective synthesis of functionalized quinolines through Vilsmeier cyclization of a variety of alpha-oxoketene-N,S-anilinoacetals has been reported. The cyclization is found to be facile with N,S-acetals bearing strongly activating groups on aniline, whereas yields of quinolines are moderate in other cases. The reaction could also be extended for the synthesis of substituted tricyclic benzo[h]quinoline, pyrido[2,3-h]quinoline, 4,7-diphenylphenanthroline, and tetracyclic quino[8,7-h]quinoline by performing a Vilsmeier reaction on N,S-acetals derived from 1-naphthylamine, m-phenylenediamine, o-phenylenediamine, and 1,5-diaminonaphthalene, respectively. A few of the newly synthesized quinolines are subjected to further transformation to afford 2-unsubstituted (Raney-Ni/Ethanol), quinoline-5,8-quinone (NBS/H(2)SO(4)), or 2-alkyl/aryl aminoquinolines through sequential m-CPBA oxidation to the corresponding (2-methylsulfonyl)quinoline followed by replacement with appropriate amines. Similarly, cycloannulation of a few 2-methylthio-3-benzoylquinolines with hydrazine hydrate under microwave irradiation afforded the corresponding substituted and fused pyrazolo[3,4-b]quinolines in excellent yields, whereas TBTH/AIBN-mediated cyclization of the corresponding 3-(2-bromobenzoyl)-2-methylthioquinolines yielded the corresponding benzothiopyrano-fused quinolines through radical translocation. 相似文献
6.
Mrityunjaya Asthana Neha SharmaRitush Kumar Jay Bahadur SinghRadhey M. Singh 《Tetrahedron letters》2014
I2-catalyzed base-free reactions of 3-homoallylquinoline-2-thiones have been described for the synthesis of tetracyclic quinolines, tetrahydrofuro [2′,4′:4,6]thiopyrano[2,3-b]quinolines in excellent yields. Similarly, I2-catalyzed reactions could proceed to tricyclic quinolines from hydroxyl group protected 3-homoallylquinoline-2-thiones. However, deprotection of group in tricyclic quinoline with HI again transformed into tetracyclic quinoline. The sulfonium salt intermediate has been proposed to explain these reactions. 相似文献
7.
Zhenhua Fan Shanxue Yang Xin Peng Cheng Zhang Jing Han Jie Chen Hongmei Deng Min Shao Hui Zhang Weiguo Cao 《Tetrahedron》2019,75(7):868-873
A facile synthesis of 2-difluoromethylated quinolines via DBU-promoted cascade Michael addition/cyclization between functionalized 2-aminobenzonitriles and methyl 4,4-difluorobut-2-ynoate has been developed. Various highly functionalized quinolines were assembled in moderate to good yields under mild metal-free reaction conditions. 相似文献
8.
A simple and efficient methodology permitting the halogenation of 2-methylquinolines into 2-(chloromethyl)quinolines or 2-(bromomethyl)quinolines in the tetrabutylammonium iodide and 1,2-dichloroethane (1,2-dibromoethane) system has been developed for the first time. The halogenation can be rapidly completed with good to excellent yields and high selectivity under microwave irradiation. 相似文献
9.
A variety of diallylanilines are shown to undergo cobalt-carbonyl catalyzed rearrangement to quinolines. Diallylanilines are also used as allyl transfer reagents to convert benzaldimines into quinolines. Substitution in the 2- and 3-positions of the quinoline is featured in all transformations. 相似文献
10.
A series of N-acyl-1, 2, 3, 4-tetrahydro-4-alkyl(aryl)iminobenzo[g]quinolines has been obtained by the condensation of N-acyl-1, 2, 3, 4-tetrahydro-4-oxobenzo[g]quinolines with primary amines.For part IV, see [1]. 相似文献
11.
Ken Motokura 《Tetrahedron letters》2004,45(31):6029-6032
The Ru-grafted hydrotalcite was found to be an excellent multifunctional catalyst for one-pot synthesis of quinolines from 2-aminobenzyl alcohol and various carbonyl compounds. These quinolines were obtained through aerobic oxidation by the Ru species, followed by aldol reaction on base sites of the hydrotalcite. 相似文献
12.
A simple and efficient (bromodimethyl)sulfonium bromide catalyzed synthesis of quinolines, by condensation of α‐amino carbonyl, that is, 2‐aminobenzophenone and 2‐aminoacetophenone with α‐methylene containing carbonyl like 1,3‐dicarbonyls has been developed. The reaction is versatile, solvent‐free protocol for generation of structurally diverse quinolines. 相似文献
13.
《中国科学:化学(英文版)》2017,(7)
N-methyl-tetrahydroquinolines(MTHQs) are a kind of very useful chemicals, which can be obtained from N-methylation of amines.However, the methylation of quinolines which is a kind of highly unsaturated nitrogen-containing heterocyclic aromatic compounds has not been reported. In this work, we report the first work for the synthesis of MTHQs by methylation of quinolines using CO_2 and H_2. It was found that Ru(acac)_3-triphos [triphos: 1,1,1-tris(diphenylphosphinomethyl)ethanl] complex was very active and selective for the N-methylation reaction of quinolines, and the yield of the desired product could reach 99%. 相似文献
14.
Reduction of secondary and tertiary o-nitrophenyl propargyl alcohols followed by acid-catalyzed Meyer-Schuster rearrangement gave 2-substituted and 2,4-disubstituted quinolines, respectively. Tertiary propargyl alcohols gave excellent yields of the quinoline derivative, while the yields of quinolines were slightly reduced when secondary propargyl alcohol derivatives were utilized. 相似文献
15.
Hongyang Zhao Yanpeng Xing Prof. Dr. Ping Lu Prof. Dr. Yanguang Wang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(42):15144-15150
Cyclopenta[b]quinolines and cyclohexa[b]quinolines were prepared via the reactions of α‐diazo ketones with N‐(2‐cyclopropylidenemethylphenyl)phosphanimines and N‐(2‐cyclobutylidenemethylphenyl) phosphanimine, respectively. The reaction proceeds in a cascade involving ketenimine formation, 6 π‐electron ring closure, and 1,3‐alkyl shift. A similar approach was developed for the synthesis of dihydropyrrolo‐[2,3‐b]quinolines from N‐(2‐cyclopropylidenemethylphenyl)phosphanimines and isocyanates. 相似文献
16.
An efficient method for the transfer hydrogenation of quinolines catalyzed by a Cp∗Ir complex was developed. A variety of 1,2,3,4-tetrahydroquinolines were obtained by regio- and chemoselective transfer hydrogenation of quinolines using 2-propanol as a hydrogen source. 相似文献
17.
A. A. Avetisyan I. L. Aleksanyan K. S. Sargsyan 《Russian Journal of Organic Chemistry》2008,44(11):1645-1648
A convenient synthetic procedure for substituted 2-bromomethyl-4-methyl-2-chloro-2,3-dihydrofuro[3.2-c]quinolines hydrobromides was developed, synthons for preparation of new substituted furoquinolines. Reactions with various nucleophiles were performed, and 2-(R’-methyl)-4-methyl-furo[3.2-c]quinolines substituted in the benzene ring were obtained. 相似文献
18.
19.
Palladium(0)/copper iodide catalyzed Sonogashira cross-coupling of 2-aryl-3-iodo-4-(phenylamino)quinolines with terminal alkynes afforded series of 1,2,4-trisubstituted 1H-pyrrolo[3,2-c]quinolines in a single-step operation. Conversely, the 4-(N,N-allylphenylamino)-2-aryl-3-iodoquinoline derivatives were found to undergo PdCl2(PPh3)2/CuI catalyzed intramolecular Heck reaction to yield the corresponding 1,3,4-trisubstituted 1H-pyrrolo[3,2-c]quinolines. 相似文献
20.
3,4-Dihydro-2H-pyrano[2,3-b]quinolines 5a-e and 2H-pyrano[2,3- b ]quinolines 10a-c were synthesised starting from the appropriate ω-chloro-n-valeroylanilides 2a-e . Compounds 10a-c were transformed to analogs of the novel antihypertensive agent Cromakalim ( 1 ). 相似文献