Synthesis of Quinoline-Fused 1-Benzazepines through a Mannich-Type Reaction of a C,N-Bisnucleophile Generated from 2-Aminobenzaldehyde and 2-Methylindole

Min, Lijun; Pan, Bin; Gu, Yanlong

doi:10.1021/acs.orglett.5b03287

Cited by 52 publications

(14 citation statements)

References 51 publications

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“…Additionally, the Lewis acid‐catalyzed formation of unexpected benzazepine‐fused quinoline synthesis was reported by Gu and co‐workers . 2‐Aminobenzaldehydes, 2‐methylindole, and acetophenone go through Lewis acid‐mediated combination process (2‐aminobenzaldehyde with 2‐methylindole), nucleophilic cyclization (combined arylamine intermediate), C−N bond cleavage (cyclized arylamine intermediate) and Mannich‐like cyclization (free arylamine intermediate attacks acetophenone) to form the benzazepine‐fused quinolines in fair to excellent yields (Scheme ).…”

Section: Synthesis Routes To Functionalized Quinolinesmentioning

confidence: 99%

“…Additionally,t he Lewis acid-catalyzed formation of unexpected benzazepine-fused quinoline synthesis was reported by Gu and co-workers. [27] 2-Aminobenzaldehydes, 2-methylindole,a nd acetophenone go through Lewis acid-mediated combination process (2-aminobenzaldehyde with 2-methylindole), nucleophilic cyclization (combined arylamine intermediate), CÀN Scheme5.Friedländer reaction starting from 2-alkynylanilines.…”

Section: Anilinederived Synthesesmentioning

confidence: 99%

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Organocatalyzed Synthesis of Functionalized Quinolines

Niu

Liang

2019

Chemistry An Asian Journal

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As one of the most widely investigated compound skeleton, quinolines possess important medicinal and biological activities. As such, ag reat number of literatures, including reviews, have reported various methodologies to construct quinolines. Recently,o rganocatalyzed reactions have attracted the attention of organic chemists due to its being "green" because the reactions avoid the use of toxic metals.I nt his review, various distinctive contributionsa re surveyed with specific emphasis on organocatalyzed reactions for quinoline core constructions.

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Section: Synthesis Routes To Functionalized Quinolinesmentioning

confidence: 99%

Section: Anilinederived Synthesesmentioning

confidence: 99%

Organocatalyzed Synthesis of Functionalized Quinolines

Niu

Liang

2019

Chemistry An Asian Journal

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“…They applied this acid catalyst to a solvent-free Friedländer reaction of 2-aminoarylketones (32) with various carbonyl compounds (33). In this way, they obtained several 2,3-disubstituted quinolines (35), including fused five-member rings, with good to excellent yields. Zhu et al [33] used p-toluenesulfonic acid as a catalyst in their pursuit of elusive 4-alkylquinolines (37, Figure 17).…”

Section: Friedländer Reactionmentioning

confidence: 99%

“…This intermediate then goes through nucleophilic Additionally, Lewis acid catalysis has featured in recent literature on the Friedländer quinoline synthesis. Gu and coworkers [35] reported the Lewis acid-catalyzed formation of unexpected benzazepine-fused quinoline products from 2-aminobenzaldehydes, 2-methylindole, and acetophenone ( Figure 19). The proposed mechanism begins with Lewis acid-mediated combination of 2-aminobenzaldehyde 39 with 2-methylindole 40.…”

Section: Friedländer Reactionmentioning

confidence: 99%

Recent Advances in Metal-Free Quinoline Synthesis

2016

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Abstract:The quinoline ring system is one of the most ubiquitous heterocycles in the fields of medicinal and industrial chemistry, forming the scaffold for compounds of great significance. These include anti-inflammatory and antitumor agents, the antimalarial drugs quinine and chloroquine, and organic light-emitting diodes. Quinolines were first synthesized in 1879, and since then a multitude of synthetic routes have been developed. Many of these methods, such as the Skraup, Doebner-Von Miller, and Friedlander quinoline syntheses, are well-known but suffer from inefficiency, harsh reaction conditions, and toxic reagents. This review focuses on recent transition metal-free processes toward these important heterocycles, including both novel routes and modifications to established methods. For example, variations on the Skraup method include microwave irradiation, ionic liquid media, and novel annulation partners, all of which have shown increased reaction efficiency and improved yield of the heteroring-unsubstituted quinoline products. Similarly, modifications to other synthetic routes have been implemented, with the quinoline products displaying a wide variety of substitution patterns.

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“…Recently, Gu et al. described the synthesis of various quinoline‐fused 1‐benzazepine derivatives 90 using the C,N‐1,6‐bisnucleophile generated in situ from a 2‐aminobenzaldehyde and 2‐methylindole through a Mannich‐type reaction (Scheme ) . After screening of various conditions, BF 3 ⋅ Et 2 O was the best catalyst and acetonitrile was found to be the optimal solvent.…”

Section: Benzaldo‐x Bifunctional Building Blocks and Their Heterocyclmentioning

confidence: 99%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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Compounds containing oxygen, nitrogen, or sulfur atoms inside the rings are attracting much attention and interest due to their biological importance. In recent years, several methods for the synthesis of such molecules have been reported by using aldo-X bifunctional building blocks (AXB3 s) as substrates; these are a wide class of organic molecules that contain at least two reactive sites, among them, one aldehyde, acetal, or semiacetal group was involved. Because of the multiple reactivities, AXB3 s are widely used in the one-pot synthesis of biologically important heterocycles. This review summarizes the synthesis of important heterocycles by using AXB3 s as pivotal components in establishing multicomponent reactions, tandem reactions, and so forth. In many cases, the established reaction systems with AXB3 s were characterized by some green properties, such as easy access to the substrate, mild and environmentally benign conditions, and wide scope of the substrate.

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Synthesis of Quinoline-Fused 1-Benzazepines through a Mannich-Type Reaction of a C,N-Bisnucleophile Generated from 2-Aminobenzaldehyde and 2-Methylindole

Abstract: Various quinoline-fused 1-benzazepine derivatives were synthesized using the C,N-1,6-bisnucleophile generated in situ from o-aminobenzaldehyde and 2-methylindole through a Mannich-type reaction.

Cited by 52 publications

References 51 publications

Organocatalyzed Synthesis of Functionalized Quinolines

Organocatalyzed Synthesis of Functionalized Quinolines

Recent Advances in Metal-Free Quinoline Synthesis

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

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