Mn(III)-based reaction of alkenes with quinolinones. Formation of peroxyquinolinones and quinoline-related derivatives

Nishino, Hiroshi; Kumabe, Ryoukou; Hamada, Ryoichi; Yakut, Mehtap

doi:10.1016/j.tet.2014.01.013

Cited by 23 publications

(9 citation statements)

References 74 publications

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“…Treatments of 1a and 1d with 1,1-diphenyl-1,3-butadiene 2c gave dihydrofuran 3h (91%) (obtained in 78% yield by Mn(OAc) 3 ) 14 and 3i (84%) in excellent yields, respectively (Entries, 7 and 8). Upon comparing the addition reactions of both compounds 2a and 2c, it is observed that diene 2c produced dihydrofuran in higher yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 2-(2-phenylethenyl) substituted 4,5-dihydrofurans by regioselective addition of 1,3-dicarbonyl compounds to dienes promoted by cerium(IV) ammonium nitrate

Yılmaz

Ustalar²

2016

Arkivoc

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Radical addition of 1,3-dicarbonyl compounds to conjugated dienes in the presence of cerium(IV) ammonium nitrate in THF produced 4,5-dihydrofurans in good to excellent yields. All radical additions occurred on the terminal double bond as regioselective. Two different dihydrofurans were obtained from the reaction of 1-phenyl-1,3-butanedione with 1-phenyl-1,3-butadiene and 3-methyl-1-phenyl-1,3-butadiene. All compounds were characterised by IR, 1 H, 13 C-NMR and HRMS spectra.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 2-(2-phenylethenyl) substituted 4,5-dihydrofurans by regioselective addition of 1,3-dicarbonyl compounds to dienes promoted by cerium(IV) ammonium nitrate

Yılmaz

Ustalar²

2016

Arkivoc

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“…3r: R 4 = H, 78% 3s: R 4 = Me, 68% 3t: R 5 = COOEt, 76% 3u: 8-(2-噻吩基 )-2,14-二氢 -1H-8,14-亚甲基苯并 [7,8]…”

Section: 随后我们将底物 4-羟基-2(1h)-喹啉酮拓展为一些unclassified

“…豆素稠合的 2,8-二氧杂双环[3.3.1]壬烷衍生物的理想溶剂 [21] . 考虑到反应底物的溶解性, 我们将 2-羟基查尔酮 (1a, 0.5 mmol)和 4-羟基-2(1H)-喹啉酮(2a, 0.5 mmol)混合于正丙醇中, 反应回流 12 h 后反应原料消失, 冷却至室温后, 发现有大量的白色固体从溶液中析出, 通过了 1 H NMR、 13 C NMR、IR 和 HRMS 的表征, 证实其结构为 8-苯基-2,14-二氢-1H-8,14-亚甲基苯并 [7,8] [1,3]二氧桥 [5,4-c]喹啉-1-酮(3a). 为了拓展该反应底物的范围, 我们尝试以各种取代的 2-羟基查尔酮 [25]…”

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Synthesis of Quinolinone- and Pyridinone-Fused Oxabicyclo[3.3.1]nonanes

叶明琰¹,

邱少中²,

殷国栋³

2017

Chin. J. Org. Chem.

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An efficient and stereoselective synthesis of quinolinone-and pyridinone-fused 2,8-dioxabicyclo[3.3.1]-nonanes by the reaction of 2-hydroxychalcones with 4-hydroxy-2(1H)-quinolinones/4-hydroxy-2(1H)-pyridinones in refluxing n-PrOH is described. The quinolinone fragment can be converted into the corresponding N-alkylated quinolinones and O-alkylated quinolines by the alkylation reaction. All the unknown compounds are characterized by means of 1 H NMR, 13 C NMR, IR and HRMS. The structures and configurations of 6-phenyl-2,12-dihydro-1H-6,12-methanobenzo[7,8][1,3]dioxocino[5,4-c]pyridin-1-one (3r) and 1-isopropoxy-8-phenyl-14H-8,14-methanobenzo[7,8][1,3]dioxocino[5,4-c]quinoline (6c) are further confirmed by X-ray single crystal diffraction analysis. Keywords 4-hydroxy-2(1H)-quinolinone; 4-hydroxy-2(1H)-pyridinone; bicyclo[3.3.1]nonane; alkylation; X-ray structure 2(1H)-喹啉酮和 2(1H)-吡啶酮是两类重要的杂环化合物, 其结构片段大量存在于许多天然的生物碱中, 如 Euodenine A、Funiculosin、Ilicicolin H 等 [1～4]. 含有这类杂环骨架的分子常常展现出良好的抗菌、抗病毒和抗癌活性 [5～7]. 4-羟基-2(1H)-喹啉酮是一个含有多官能团的分子, 羟基和氨基都容易参与反应, 3-位碳原子也具有很好的亲核性, 因此被广泛应用于合成一些功能化的杂环化合物 [8～10]. 此外, 双环[3.3.1]壬烷是一种具有 V-型结构的迷人分子 [11,12] , 它们在药物化学和分子识别中表现出潜在的应用价值 [13,14] , 因此, 这类化合物的制备与功能化近年来受到了化学家的持续关注 [15～20]. 在最近的研究中, 我们发展了一种以 2-羟基查尔酮与六元环状的 1,3-二酮(或萘酚/取代苯酚)高立体选择性地合成 2,8-二氧杂双环[3.3.1]壬烷的新方法 [21～23]. 然而, 目前鲜有文献引入含氮芳香环于此类结构中 [24] , 此处我们进一步将反应底物拓展为 4-羟基-2(1H)-喹啉酮和 4-羟基-2(1H)-吡啶酮衍生物, 立体选择性地合成了系列新型含有喹啉酮和吡啶酮稠合的 2,8-二氧杂双环[3.3.1]壬烷, 并发现前者与卤代烷烃反应, 喹啉酮片段可有效地转化为相应的氮烷基取代的喹啉酮和氧烷基取代的喹啉结构.

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“…19 Thus, an efficient synthesis of these compounds has been of great interest in past years. 20 There have been developed different methods of synthesis for 2,3-dihydroquinazolin-4(1H)-ones (DQZ) most recently; Mn III -based reaction, 21 under ultrasonic irradiation, 22 zeolite catalyzed method, 23 with green chemistry using nanoindium oxide 24 and carbon nanotubes as a heterogeneous catalyst, 25 etc. [26][27][28][29][30][31] QZ skeleton is very common in many natural alkaloids.…”

Section: Introductionmentioning

confidence: 99%

Eco-Friendly Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones Catalyzed by FeCl3/Al2O3 and Analysis of Large 1 H NMR Diastereotopic Effect

Monreal¹,

Sánchez-Castellanos²,

Ramírez-Gualito³

et al. 2018

J. Braz. Chem. Soc.

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In the present study, we have carried out a condensation reaction for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones from 2-amino-N-benzylbenzamide and different aromatic aldehydes using FeCl 3 catalyst supported on Al 2 O 3. It was demonstrated that this material can be used successfully for the nucleation of quinazolinones with good to excellent yield; furthermore, the FeCl 3 /Al 2 O 3 catalyst can be recovered and reused. This catalyst was used before in the synthesis of imidazole with very good yields. The synthesized quinazolinones showed a large range diastereotopic effect over the methylene group and, this anomalous difference was studied through nuclear magnetic resonance (NMR) and computational calculations.

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Mn(III)-based reaction of alkenes with quinolinones. Formation of peroxyquinolinones and quinoline-related derivatives

Cited by 23 publications

References 74 publications

Synthesis of 2-(2-phenylethenyl) substituted 4,5-dihydrofurans by regioselective addition of 1,3-dicarbonyl compounds to dienes promoted by cerium(IV) ammonium nitrate

Synthesis of 2-(2-phenylethenyl) substituted 4,5-dihydrofurans by regioselective addition of 1,3-dicarbonyl compounds to dienes promoted by cerium(IV) ammonium nitrate

Synthesis of Quinolinone- and Pyridinone-Fused Oxabicyclo[3.3.1]nonanes

Eco-Friendly Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones Catalyzed by FeCl3/Al2O3 and Analysis of Large 1 H NMR Diastereotopic Effect

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