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1.
The superelectrophilic activation of N-aryl amides of 3-arylpropynoic acids by Bronsted superacids (CF3SO3H, HSO3F) or strong Lewis acids AlX3 (X=Cl, Br) results in the formation of 4-aryl quinolin-2(1H)-ones in quantitative yields. The vinyl triflates or vinyl chlorides may be formed as additional reaction products. The investigated amides in reactions with benzene give 4,4-diaryl 3,4-dihydroquinolin-2-(1H)-ones under the superelectrophilic activation. 4-Aryl quinolin-2(1H)-ones in POCl3 are converted into 4-aryl 2-chloroquinolines. 4-Fluorophenyl-4-phenyl 3,4-dihydroquinolin-2-(1H)-one give N-formylation products in a yield of 79% under the Vilsmeier–Haack reaction conditions. 相似文献
2.
Vakhid A. Mamedov Elena A. Khafizova Victor V. Syakaev Aidar T. Gubaidullin Aida I. Samigullina Nataliya E. Algaeva Shamil K. Latypov 《Tetrahedron》2018,74(45):6544-6557
A new and highly efficient method for the synthesis of 4-(benzimidazol-2-yl)quinolin-2(1H)-ones via the rearrangement of spiroquinoxalinones in moderate-to-excellent yields has been developed. The rearrangement represents a facile approach to medicinally important biheterocyclic compounds. Compared to other methods, the present protocol has a number of advantages such as – cost-effectiveness, avoidance of difficult of access quinolin-2-one and benzimidazole derivatives as reaction partners, and easy accessibility of starting materials, making it a highly practical approach to access various 4-(benzimidazol-2-yl)quinolin-2(1H)-ones. 相似文献
3.
Representatives of the 3H-imidazo[4,5-c]quinolin-4(5H)-ones have shown interesting biological activity. We have found 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-one as a potent dipeptidyl peptidase 4 inhibitor. However effective synthesis of this nucleus with various substituents at the 6-9-positions has not been reported. We report herein the development of a novel and efficient synthesis of 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-ones by palladium-assisted internal biaryl coupling reaction. Our optimization of the reaction conditions revealed that the most important factors for this reaction are use of silver carbonate as a base and high reaction temperature. 相似文献
4.
Nina A. Larina Jerome Berthet Gaston Vermeersch Vladimir Khodorkovsky 《Tetrahedron》2010,66(42):8291-8299
Synthesis and characterization of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones is described. In addition to their potential biological activity, these compounds exhibit photoreversible photochromic properties in anaerobic conditions. Using the 1 and 2D NMR techniques we demonstrated that the coloration occurred owing to the formation of fluorescent 5a,6-dihydrobenzo[b]acridin-(5H)-ones. The photoreaction is stereoselective and the S,R-isomers are the major products (83%) whereas the S,S-isomers are the minor (6%). In addition, the irreversible formation of two oxidation products, 3-(2-benzoylbenzoyl)quinolin-4(1H)-ones, and acridin-12(5H)-one derivatives was observed in the presence of air. 相似文献
5.
N-Alkyl-4-alkoxy-3-alkynylpyridin-2(1H)-ones readily undergo acid-promoted 5-endo-heteroannulation to furopyridinium intermediates that are dealkylated in situ to provide the corresponding furo[2,3-b]pyridin-4(7H)-ones. The same strategy applies to the formation of furo[2,3-b]quinolin-4(9H)-ones. In the case of Me3Si-substituted alkynes, hydration of the triple bond was observed. 相似文献
6.
Pd(PPh3)4 catalyzed Suzuki-Miyaura cross-coupling reactions of 4-tosyloxycoumarins or 4-tosyloxyquinolin-2(1H)-one with various potassium aryl trifluoroborates afforded the corresponding 4-substituted coumarins or 4-substituted quinolin-2(1H)-ones in good to excellent yield. 相似文献
7.
Substituted cyclopenta[b]quinolin-1-ones were prepared by thermal ring-expansion of substituted N-Boc protected 4-(2-aminophenylethynyl)-4-hydroxy-2-cyclobuten-1-ones forming the corresponding 2-aminophenylmethylidene substituted 4-cyclopentene-1,3-diones. Deprotection of the amine resulted in spontaneous condensation giving cyclopenta[b]quinolin-1-ones. Sodium borohydride reduction of these products produced cyclopenta[b]quinolin-1-ols. 相似文献
8.
En-Chiuan Chang Ya-Lan Wen Chun-Hsi Chang Yun-Hwei Shen Shaw-Bing Wen Mou-Yung Yeh Fung Fuh Wong 《Tetrahedron》2012,68(29):5920-5924
Two regioisomers of 2-arylpyrazolo[3,4-c]quinolin-4(5H)-ones and 2-arylpyrazolo[4,3-c]quinolin-4(5H)-ones were synthesized by utilizing 3-arylsydnones, ethyl 3-bromopropynoate, and 2-aminophenylboronic acid pinacol ester in presence of catalytic agent Pd(PPh3)4. This efficient one-pot synthesis methodology involved 1,3-dipolar cycloaddition, Suzuki coupling reaction, and intramolecular cyclization three sequence steps. 相似文献
9.
Helio G. Bonacorso Rogerio V. Lourega Everton D. Deon Nilo Zanatta Marcos A.P. Martins 《Tetrahedron letters》2007,48(28):4835-4838
The first synthesis of a series of 2-aryl(heteroaryl)-4-trifluoromethyl-4,5-dihydro-3H-pyrido[2,3-b][1,4]diazepin-4-ols, where aryl = C6H5, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-CH3C6H4, 4-OCH3C6H4, 4,4′-biphenyl, 1-naphthyl and heteroaryl = 2-thienyl, 2-furyl obtained from the direct cyclocondensation reaction of 4-methoxy-1,1,1-trifluoroalk-3-en-2-ones with 2,3-diaminopyridine in 54-71% yield, is reported. Another alternative and efficient route for the synthesis of a series of 2-aryl(heteroaryl)-3H-pyrido[2,3-b][1,4]diazepin-4(5H)-ones from the reaction 4-methoxy-1,1,1-trichloroalk-3-en-2-ones with 2,3-diaminopyridine, in 54-70% yield, is also reported. 相似文献
10.
Alexander V. Stepakov Michail A. KinzhalovVitaly M. Boitsov Liubov V. StepakovaGalina L. Starova Sergey Yu. VyazminElena V. Grinenko 《Tetrahedron letters》2011,52(24):3146-3149
Reaction of N-aryl substituted maleimides with aliphatic ketazines leads to the formation of 4,5-dihydropyridazin-3(2H)-ones in moderate yields. The reaction proceeds through 1,4-addition of an azine to the maleimide double bond, as confirmed by separation of the corresponding adducts in some cases, which are then converted into 4,5-dihydropyridazin-3(2H)-ones. In addition, the solid-state synthesis of 4,5-dihydropyridazin-3(2H)-ones is demonstrated for the first time. 相似文献