Efficient synthesis of 2-acylquinolines based on an aza-vinylogous Povarov reaction

文献情報

出版日 2016-02-15

DOI 10.1039/C6QO00037A

インパクトファクター 5.281

著者

Giulia Bianchini, Pascual Ribelles, M. Teresa Ramos, J. Carlos Menéndez

原文を見る

要旨

The aza-vinylogous Povarov reaction between α-ketoimines and α,β-unsaturated dimethylhydrazones in the presence of indium trichloride affords 2-acyl-4-alkyl-4-dimethylhydrazonomethyl-1,2,3,4-tetrahydroquinolines with good cis/trans diastereoselectivities. These compounds were readily transformed into highly substituted 2-acylquinolines using a two-reaction sequence involving the oxidative generation of a C-4 nitrile group, followed by its elimination under thermal conditions. Alternatively, a one-pot protocol based on the reaction of hydrazones with magnesium monoperoxyphthalate hexahydrate in refluxing methanol afforded the target 2-acylquinolines in good to excellent yields. This methodology was also extended to the preparation of 2-arylquinolines.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Efficient synthesis of 2-acylquinolines based on an aza-vinylogous Povarov reaction

文献情報

おすすめジャーナル

関連文献

An umpolung strategy for chemoselective metal-free [4 + 2] annulation of azlactones: access to tetrahydro-β-carbolin 1,3-diketone frameworks

Synthesis of 2-acyl benzofurans and indoles based on nucleophile-intercepted Meyer–Schuster rearrangement of o-hydroxyphenyl and o-aminophenyl propargylic alcohols

Practical synthesis and divergent optimization of halichonine B for the discovery of novel pharmaceutical leads

Polycyclic aromatic hydrocarbons containing antiaromatic chalcogenopyrano[3,2-b]-chalcogenopyrans

Copper-catalyzed crosscoupling of vinyl nitrenes and CF3-carbenes to synthesize CF3-2-azadienes

Inside front cover

Radical-triggered base-free 1,3-C → C migrations: chemodivergent synthesis of cyclic imines from N-allyl enamines

Gold catalyzed spirocyclization of 1-ene-4,9- and 3-ene-1,7-diyne esters to azaspiro[4.4]nonenones and azaspiro[4.5]decadienones

Sequential annulation of bidentate diamines for modular access to N-fused/helical/spiro-carbazole scaffolds

Electrochemical synthesis of CN-substituted imidazo[1,5-a]pyridines via a cascade process using NH4SCN as both an electrolyte and a non-trivial cyanating agent

こちらもおすすめ

6-苄基-6,7-二氢-5H-吡咯并3,4-b吡啶とは何ですか？

半硫酸奎宁单水水合物はどのように保存すればよいですか？

D-核糖-5-リン酸二ナトリウムとは何ですか？

異丙基肼はどの業界で使用されていますか？

3-乙酰基-4-羟基喹啉-2(1H)-酮はどのように合成されますか？

Bobcat339はどのように保存すればよいですか？

5-溴-4-甲基-1H-吲唑とは何ですか？

3-(4メトキシフェニル)オキテナン-3カーボイル酸の代替品はありますか？

3-イリドオキシピロロ[2,3-b]ピリジン-5-カルボキシlic酸は安全ですか？

3-氟-4- iodobenolを取り扱う際の実験室安全事項は何ですか？

掲載誌

Organic Chemistry Frontiers

おすすめ化合物

3,5-Dichloro-4-hydrazinopyridine

[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acid

N-(4-Chlorobenzyl)-beta-alanine hydrochloride (1:1)

1-(3,4-Dichlorophenyl)-1H-pyrazole-3-carboxylic acid

tert-Butyl 6-chloro-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate

おすすめサプライヤー