Synthesis of Highly Functionalized 4‐Aminoquinolines

Wezeman, Tim; Zhong, Sabilla; Nieger, Martin; Bräse, Stefan

doi:10.1002/anie.201511385

Cited by 50 publications

(26 citation statements)

References 57 publications

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“…Although it is known that terminal sulfonyl ynamides are water sensitive, this was not a major concern during previous studies on metal-free systems, as the desired reactions outpaced any side-reactions. 34 However, during our copper catalyst screen, we found that the presence of the copper promoters facilitated the hydrolysis of the terminal sulfonyl ynamide 1a to its sulfonyl amide 2 (Scheme 1).…”

Section: -32mentioning

confidence: 98%

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Synthesis of aminopyrazoles from sydnones and ynamides

et al. 2017

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Section: -32mentioning

confidence: 98%

“…34 Alternative popular synthetic routes to ynamides include copper-catalysed amidative cross-coupling processes. [35][36][37][38][39][40][41][42][43] The sydnones could be accessed via a two-step procedure consisting of the nitrosation and cyclodehydration of Narylglycines, as extensively reported in the literature.…”

Section: -32mentioning

confidence: 99%

Synthesis of aminopyrazoles from sydnones and ynamides

et al. 2017

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“…Recent further work on this family of transformations has led to the development of highly modular processes, allowing access to a wide range of heterocyclic structures. 42,43 While the aforementioned processes hinge on the addition of a two-carbon nucleophilic moiety, affording six-membered rings, Wang et al were able to elegantly utilise ethyl diazoacetate (EDA) as a one-carbon synthon (Scheme 14). 44 Forming substituted indole products (62), the authors exploited the inherent ambiphilic properties of EDA initially attacking the electrophilic nitrilium ion 60 and subsequently undergoing displacement of dinitrogen during cyclisation.…”

Section: Intermolecular Addition Of Carbon Nucleophilesmentioning

confidence: 99%

Amide activation: an emerging tool for chemoselective synthesis

et al. 2018

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It is textbook knowledge that carboxamides benefit from increased stabilisation of the electrophilic carbonyl carbon when compared to other carbonyl and carboxyl derivatives. This results in a considerably reduced reactivity towards nucleophiles. Accordingly, a perception has been developed of amides as significantly less useful functional handles than their ester and acid chloride counterparts. However, a significant body of research on the selective activation of amides to achieve powerful transformations under mild conditions has emerged over the past decades. This review article aims at placing electrophilic amide activation in both a historical context and in that of natural product synthesis, highlighting the synthetic applications and the potential of this approach.

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“…They obtained many 4-sulfonylamino quinolines (73) in good yield, which could then be easily converted to biologically useful amines by hydrolysis of the protecting group. Finally, Bräse and coworkers [45] described the synthesis of functionalized quinolines from sulfanyl ynamides 72 and electrophilically-activated aryl amides 71 under the influence of triflic anhydride and 2-chloropyridine ( Figure 32). Inspired by the work of Movassaghi, who developed this method to synthesize pyridine, pyrimidine, and β-carboline derivatives, the Bräse group applied this procedure to quinoline synthesis.…”

Section: Electrophilic Cyclizationmentioning

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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Synthesis of Highly Functionalized 4‐Aminoquinolines

Abstract: A diverse set of highly substituted 4-aminoquinolines was synthesized from ynamides, triflic anhydride, 2-chloropyridine, and readily accessible amides in a mild one-step procedure.

Cited by 50 publications

References 57 publications

Synthesis of aminopyrazoles from sydnones and ynamides

Synthesis of aminopyrazoles from sydnones and ynamides

Amide activation: an emerging tool for chemoselective synthesis

Recent Advances in Metal-Free Quinoline Synthesis

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