Synthesis of Fused Quinoline and Quinoxaline Derivatives Enabled by Domino Radical Triple Bond Insertions

Sun, Xiaoyang; Li, Jiahong; Ni, Yunpeng; Ren, Daan; Hu, Zhentao; Yu, Shouyun

doi:10.1002/ajoc.201402222

Cited by 39 publications

(27 citation statements)

References 94 publications

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“…In 2014, Yu'sg roup employed alkyne-derived a-bromocarbonyl compounds and isocyanides as reactions ubstrates in a photocatalytic bicyclization cascade reaction, which allowed regioselectivea ccess to fused quinoline derivatives 93 and 93' in good-to-excellent yields (Scheme 26 a). [46] Regioselectivities of between4 .6:1 and 10.8:1 were obtained when ap henyl group was installed at the para position of the phenyli socyanide. This reaction was appliedt ot he synthesis of quinoxaline derivatives through ap hotocatalytic radicalb icyclization reaction between isocyanides and cyano-derived a-bromocarbonyl compounds.…”

Section: Bicyclization Reactions Of Reactants With Radical Donor-accementioning

confidence: 99%

Recent Advances in Radical‐Enabled Bicyclization and Annulation/1,n‐Bifunctionalization Reactions

Huang

Hao

Jiang

2018

Chemistry An Asian Journal

141

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Over the past few years, the development of new radical reactions has gained considerable momentum. Most such radical transformations heavily depend on the in situ generation of reactive radical species, initiated by oxidants, metal salts, visible-light photocatalysis, or electrocatalysis. In this context, numerous radical-enabled bicyclization and annulation/1,n-bifunctionalization reactions have been developed, thereby providing efficient synthetic strategies for the assembly of functionalized cyclic rings that contain both heterocyclic and isocyclic skeletons. In this Focus Review, we highlight recent progress in this rapidly growing area by presenting a series of catalytic oxidative reactions, along with their reaction mechanisms and applications.

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Section: Bicyclization Reactions Of Reactants With Radical Donor-accementioning

confidence: 99%

Recent Advances in Radical‐Enabled Bicyclization and Annulation/1,n‐Bifunctionalization Reactions

Huang

Hao

Jiang

2018

Chemistry An Asian Journal

141

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“…Yu's group disclosed a visible‐light‐promoted method for the synthesis of fused quinoline 123 and quinoxaline derivatives 125 in which the imidoyl radicals were trapped by triple bonds (Scheme ) . Generally, the addition of an imidoyl radical into a nitrile group is less efficient than its addition to alkynes.…”

Section: The Synthesis Of N‐containing Heterocyclic Ringsmentioning

confidence: 99%

Synthesis ofN-Containing Heterocyclic Compounds Using Visible-light Photoredox Catalysis

Zhou

Hossain

Xiao

2016

The Chemical Record

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Nitrogen heterocycles represent a highly important class of compounds which are widely used in materials science, agrochemistry, and medicinal chemistry. Therefore, there is continuing interest in the development of convenient, efficient, and environmentally benign synthetic methods for the construction of nitrogen containing heterocycles. Due to its natural abundance, ease of use, and promising application in industry, the use of visible light as a driving force for chemical reactions has received considerable attention in the past few years. This account summarizes the synthesis of N-heterocycles using visible-light photoredox catalysis published in the last two years, according to the size and type of the formed N-heterocyclic rings. In the context of seminal works of others in this area, a concise summary of the contributions of the authors is also offered.

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“…[22] Along these lines,t he groups of Nanni and Curran disclosed ar adical cascade for the synthesis of quinoxalines starting from monoisocyanoarenes. [23] Despite intensive investigations, group or atom transfer additions to isonitriles are nearly unexplored. In arare example,Yamago and Yoshida reported radical PhTegroup transfer processes with aryl isocyanides as the acceptors.…”

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confidence: 99%

Iodinated (Perfluoro)alkyl Quinoxalines by Atom Transfer Radical Addition Using ortho‐Diisocyanoarenes as Radical Acceptors

Leifert

Studer

2016

Angew Chem Int Ed

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A simple method for the preparation of functionalized quinoxalines is reported. Starting from readily accessible ortho-diisocyanoarenes and (perfluoro)alkyl iodides, the quinoxaline core is constructed during (perfluoro)alkylation by atom transfer radical addition (ATRA), resulting in 2-iodo-3-(perfluoro)alkylquinoxalines. The radical cascades are readily initiated either with visible light or by using α,α'-azobisisobutyronitrile (AIBN). The heteroarene products are obtained in high yields (up to 94 %), and the method can be readily scaled up. Useful follow-up chemistry documents the value of the novel radical quinoxaline synthesis.

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Synthesis of Fused Quinoline and Quinoxaline Derivatives Enabled by Domino Radical Triple Bond Insertions

Cited by 39 publications

References 94 publications

Recent Advances in Radical‐Enabled Bicyclization and Annulation/1,n‐Bifunctionalization Reactions

Recent Advances in Radical‐Enabled Bicyclization and Annulation/1,n‐Bifunctionalization Reactions

Synthesis ofN-Containing Heterocyclic Compounds Using Visible-light Photoredox Catalysis

Iodinated (Perfluoro)alkyl Quinoxalines by Atom Transfer Radical Addition Using ortho‐Diisocyanoarenes as Radical Acceptors

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