Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy

Willumstad, Thomas P.; Boudreau, Paul D.; Danheiser, Rick

doi:10.1021/acs.joc.5b01648

Cited by 40 publications

(11 citation statements)

References 76 publications

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“…52 The reaction of diazo ketones 107 with N-propargyl substituted ynamides 108 proceeds via a cascade reactions to generate intermediate 109, which subsequently generate substituted aniline derivatives 110 by 6π electrocyclization. 52 The reaction of diazo ketones 107 with N-propargyl substituted ynamides 108 proceeds via a cascade reactions to generate intermediate 109, which subsequently generate substituted aniline derivatives 110 by 6π electrocyclization.…”

Section: Scheme 36mentioning

confidence: 99%

Iodine-mediated synthesis of heterocycles via electrophilic cyclization of alkynes

2016

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Iodine has been recognized as an efficient, non-toxic, readily available and easy-to-handle electrophilic reagent to favour halocyclization reactions for the synthesis of novel iodofunctionalized heterocyclic molecules that serve as versatile intermediates in synthetic organic chemistry. This review presents numerous useful methodologies for the synthesis of O, N, S, and Se-heterocycles through electrophilic cyclization via the attack of an electrophile on the C(sp) bond of alkynes. The cyclization proceeds under mild reaction conditions and tolerates a wide variety of functional groups.

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Section: Scheme 36mentioning

confidence: 99%

Iodine-mediated synthesis of heterocycles via electrophilic cyclization of alkynes

2016

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“…An elaborate strategy toward highly substituted quinolines involving benzannulation/iodocyclization steps developed by Danheiser and co‐workers in 2015 . The photochemical Wolff rearrangement forms transient vinylketene intermediate, then affords a new cyclobutenone through [2+2] cycloaddition, the dienylketene is generated through intermediate subsequently and rapid cyclization via 6‐π electrocyclic ring closure happens to furnish the desired aminophenol ring.…”

Section: Synthesis Routes To Functionalized Quinolinesmentioning

confidence: 99%

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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“…In this way, they were able to obtain various 2-thioquinolines 64 in good to excellent yield. Danheiser and coworkers [43] developed an elaborate two-stage benzannulation/iodocyclization strategy toward highly substituted quinolines (Figure 30). The first stage involves the photochemical Wolff rearrangement of α,β-unsaturated α-diazo ketones 65 to transient vinylketenes.…”

Section: Electrophilic Cyclizationmentioning

confidence: 99%

“…Upon introduction of an electrophile such as I2, the alkyne appendage performs electrophilic cyclization with the aromatic ring, affording quinolines with multiple functionalities (68). Danheiser and coworkers [43] developed an elaborate two-stage benzannulation/iodocyclization strategy toward highly substituted quinolines (Figure 30 Danheiser and coworkers [43] developed an elaborate two-stage benzannulation/iodocyclization strategy toward highly substituted quinolines (Figure 30). The first stage involves the photochemical Wolff rearrangement of α,β-unsaturated α-diazo ketones 65 to transient vinylketenes.…”

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 Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy

Cited by 40 publications

References 76 publications

Iodine-mediated synthesis of heterocycles via electrophilic cyclization of alkynes

Iodine-mediated synthesis of heterocycles via electrophilic cyclization of alkynes

Organocatalyzed Synthesis of Functionalized Quinolines

Recent Advances in Metal-Free Quinoline Synthesis

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