Au-Catalyzed Synthesis of Thiopyrano[2,3-<i>b</i>]indoles Featuring Tandem Rearrangement and Hydroarylation

Jha, Mukund; Dhiman, Shiv; Cameron, T. Stanley; Kumar, Dalip; Kumar, Anil

doi:10.1021/acs.orglett.7b00617

Cited by 27 publications

(6 citation statements)

References 42 publications

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“…This implies that enyne tethered indole sulfides 94 undergo a tandem σ-bond migration/ 6-endo-trig cyclization/oxidative aromatization process. The authors highlight the significance of the Z orientation of the C=C bond to assist the rearrangement step (Figure 9C) (Jha et al, 2017).…”

Section: Gold-catalyzed Isomerization Processes Involving An Initimentioning

confidence: 95%

Gold-Catalyzed Homogeneous (Cyclo)Isomerization Reactions

2019

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Gold is currently one of the most used metals in organometallic catalysis. The ability of gold to activate unsaturated groups in different modes, together with its tolerance to a wide range of functional groups and reaction conditions, turns gold-based complexes into efficient and highly sought after catalysts. Natural products and relevant compounds with biological and pharmaceutical activity are often characterized by complex molecular structures. (Cyclo)isomerization reactions are often a useful strategy for the generation of this molecular complexity from synthetically accessible reactants. In this review, we collect the most recent contributions in which gold(I)- and/or gold(III)-catalysts mediate intramolecular (cyclo)isomerization transformations of unsaturated species, which commonly feature allene or alkyne motifs, and organize them depending on the substrate and the reaction type.

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Section: Gold-catalyzed Isomerization Processes Involving An Initimentioning

confidence: 95%

Gold-Catalyzed Homogeneous (Cyclo)Isomerization Reactions

2019

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“…In addition, 147 could be further transformed into tetracyclic heteroaromatic isothiochromeno[1,8,7-bcd]indole 148 through a palladium-catalyzed intramolecular Heck-type crosscoupling. [55] Kumar, Jha, and co-workers reported a synthetic procedure to construct 5H-benzothiazino CÀ N or CÀ C coupling, respectively (Scheme 39a). As a result, the desired indole-fused sulfur-containing cyclized products 151 or 152 were delivered in moderate to good yields.…”

Section: Catalytic Reactionsmentioning

confidence: 99%

“…Then, the Au(III)‐catalyzed cascade skeletal rearrangement/ hydroarylation/oxidative aromatization occurred, and the tricyclic indole‐fused scaffolds 146 and 147 were obtained in good yields (Scheme 38b). In addition, 147 could be further transformed into tetracyclic heteroaromatic isothiochromeno[1,8,7‐ bcd ]indole 148 through a palladium‐catalyzed intramolecular Heck‐type cross‐coupling [55] …”

Section: ‐Thioxoindolines As Starting Materialsmentioning

confidence: 99%

Construction of Indole‐Fused Heterocycles Starting from 2‐Thioxoindolines, Iminoindolines, and Their Derivatives

Zhao

Gou

et al. 2021

Adv Synth Catal

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Indole-based heterocycles containing sulfur or nitrogen atoms are important frameworks that occur widely in biological active natural products and drugs. Consequently, several novel chemical transformations and new catalytic strategies have been developed for the preparation of these skeletons in a highly efficient and selective manner. This review focuses on recent advancements in the construction of indole-fused heterocyclic compounds by using iminoindolines, 3-diazoindol-2-imines, 2-thioxoindolines, and their derivatives as starting materials.

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“…Oxidativer earomatization of IV yieldingt he final product V (Scheme 157). [180] Very recently Park and co-workersr eported trifluoromethanesulfonic-acid-mediated cycloisomerizationso fi ndole-tethered enynes (Scheme158). Depending upon the substitution of the C3 position of indole, two divergent products wereo btained.S ubstrates with electron-withdrawing groups resulted in the formation of pyrrolo[3,2,1-ij]quinolines 620 via as elective 6-endo-dig cyclization process whereas substrates bearing sulfonyl groups at indole C3 positiony ielded benzo[3,4]azepino[1,2-a]indoles 621 following a7 -endo-dig cyclization step.…”

Section: Metamorphosis Of Heteroarene-tethered Enynesmentioning

confidence: 99%

Heteroarene‐tethered Functionalized Alkyne Metamorphosis

Bag

Sawant

2020

Chemistry A European J

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Heteroarene-tethered functionalized alkynes are multipotents ynthons in organic chemistry.T his detailed Review described herein offers at horough discussion of the metamorphosis of heteroarene-tethered functionalized alkynes, an area which has earned much attention over the past decade in the straightforward synthesis of architecturally complex heterocyclics caffolds in atom and step economic manner.D epending upon the variety of functionalized al-kynes, this Review is divided into multiple sections. Amongst the vast array of synthetic transformations covered, dearomatizings pirocyclizations and cascades pirocyclization/rearrangementa re of great interest. Synthetic transformations involving the heteroarene-tethered functionalized alkynes with scope, challenges, limitations, mechanism, their application in the total synthesis of natural products and future perceptionsa re surveyed. [a] D. Bag, Prof.

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Au-Catalyzed Synthesis of Thiopyrano[2,3-b]indoles Featuring Tandem Rearrangement and Hydroarylation

Cited by 27 publications

References 42 publications

Gold-Catalyzed Homogeneous (Cyclo)Isomerization Reactions

Gold-Catalyzed Homogeneous (Cyclo)Isomerization Reactions

Construction of Indole‐Fused Heterocycles Starting from 2‐Thioxoindolines, Iminoindolines, and Their Derivatives

Heteroarene‐tethered Functionalized Alkyne Metamorphosis

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