Efficient construction of pyrrolo[1′,2′:1,2]azocino[4,5-c]quinolines via cascade cycloaddition and annulation reaction

文献情報

出版日 2019-09-04

DOI 10.1039/C9QO00891H

インパクトファクター 5.281

著者

Wen-Tao Wu, Ying Han, Jing Sun, Chao-Guo Yan

原文を見る

要旨

Novel polysubstituted pyrrolo[1′,2′:1,2]azocino[4,5-c]quinolines were efficiently synthesized by a one-pot three-component reaction of proline, isatins and chalcones in refluxing methanol and by a sequential domino annulation reaction with methyl propiolate in refluxing acetonitrile. The reaction with isatins without an N-protecting group afforded hexahydropyrrolo[1′,2′:1,2]azocino[4,5-c]quinolines, while the reaction with N-benzylisatins gave octahydropyrrolo[1′,2′:1,2]azocino[4,5-c]quinolones with an additional propiolate unit connecting to a dihydropyridyl ring. The reaction mechanism with domino [3 + 2]cycloaddition, ring-expansion and annulation processes was rationally proposed for the formation of polycyclic products.

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 construction of pyrrolo[1′,2′:1,2]azocino[4,5-c]quinolines via cascade cycloaddition and annulation reaction

文献情報

おすすめジャーナル

関連文献

Ground and excited state properties of furanoflavylium derivatives

Adsorption of H2 on amorphous solid water studied with molecular dynamics simulations

Ab initio spectroscopy of water under electric fields

MARTINI-based simulation method for step-growth polymerization and its analysis by size exclusion characterization: a case study of cross-linked polyurethane

Correction: Predictable spectroscopic properties of type-II ZnTe/CdSe nanocrystals and electron/hole quenching

Boron-based inorganic heterocyclic clusters: electronic structure, chemical bonding, aromaticity, and analogy to hydrocarbons

Seeking minimum entropy production for a tree-like flow-field in a fuel cell

BOKEI: Bayesian optimization using knowledge of correlated torsions and expected improvement for conformer generation

Molecular dynamics investigations of oligosaccharides recognized by family 16 and 22 carbohydrate binding modules

Correction: Thermo-orientation in fluids of arbitrarily shaped particles

こちらもおすすめ

3-(2-オキサプロピル)ベンzoic酸はどのように合成されますか？

BOC-L-3-氟苯丙氨酸の主な用途は何ですか？

4-メチル-4-ピペリジニル-1-ピロリドイン甲酸の主な用途は何ですか？

Biotin-PEG3-oxyamine HCl塩について、適切な化合物名称に適用される法規ガイドラインは何ですか？

N-(4-イソチオシアネートフェニル)-2-メトキシアリニンはどのように合成されますか？

金粉蕨亭2'-O-葡萄糖甙の主な用途は何ですか？

2-(2-ニトロフェニル)酢酸ヒドライドの物理化学的性質は何ですか？

5-(ヒドロキシメチル)-2-チオキソ-2,3-ジヒドロピリミジン-4(1H)-オンを取り扱う際の実験室安全事項は何ですか？

11-脱氢血栓烷 b2の市場動向や研究トレンドはどうですか？

3,3-二甲基哌啶-4-酮はどのように保存すればよいですか？

掲載誌

Organic Chemistry Frontiers

おすすめ化合物

trans-2-(2-Methoxyphenyl)-5-oxotetrahydrofuran-3-carboxylic acid

(2E)-4-[(1R,2S,8R,19S,21R)-14-Hydroxy-11-isopropenyl-8,23,23-trimethyl-5-(3-methyl-2-buten-1-yl)-16,20-dioxo-3,7,22-trioxaheptacyclo[17.4.1.1~8,12~.0~2,17~.0~2,21~.0~4,15~.0~6,13~]pentacosa-4(15),5,13 ,17-tetraen-21-yl]-2-methyl-2-butenoic acid

4-Iodopentylbenzene

(R)-2-(Methylamino)propanoic acid hydrochloride

Benzyl spiro[indole-3,4'-piperidine]-1(2H)-carboxylate hydrochloride (1:1)

おすすめサプライヤー