Direct Synthesis of Structurally Divergent Indole Alkaloids from Simple Chemicals

Shen, Tao; Zhu, Bencong; Lin, Fengguirong; Pan, Jun; Wei, Jialiang; Luo, Xiaoling; Liu, Jianzhong; Jiao, Ning

doi:10.1002/cjoc.201800258

Cited by 21 publications

(7 citation statements)

References 65 publications

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“…Similarly, Jia group reported a metal‐free approach for the synthesis of diverse structural motifs of indole alkaloids (tryptamines, tryptamine‐related oximes, lactams, and lactones as well as β‐carbolines, spiroindolines, and hexahydropyrrolo[2,3‐ b ]indoles) where TBN as a multitask reagent. The readily available starting materials, 2‐vinylanilines, alkynes, and TBN, were used as appropriate synthons for the synthesis of complex arrays through the formation of 4–5 distinct bonds via this substrate fragmentation and cycloaddition strategy …”

Section: Outlines Of the Reactions Involving Tbnmentioning

confidence: 99%

“…2019, 14,4454 -4492 www.chemasianj.org able startingm aterials, 2-vinylanilines, alkynes, and TBN, were used as appropriate synthons for the synthesis of complex arrays through the formation of 4-5 distinct bonds via this substrate fragmentation and cycloaddition strategy. [146] In 2019 Song group reported an Au-catalyzed synthesis of 5oxazole ketones (156)f rom intramolecular cyclization of internal N-propargylamides (155)u sing TBN and 4-MeO-TEMPO. This methodology shows excellent functional group tolerance under mild conditions.…”

Section: Miscellaneousmentioning

confidence: 99%

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tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Dahiya

Sahoo

Alam

et al. 2019

Chemistry An Asian Journal

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The upsurge interesti nt he development of efficient methodologies for the constructiono fn itrogen-containing frameworks via the use of expedient reagents have been creating ar enaissance in contemporary organic chemistry.I nt his perspective, tertbutyl nitrite (TBN) is an emerging building block. Due to its uniques tructuralf eatures, it shows differential reactivity under different reaction conditions. These diverse reactivities have resulted in the construction of ad iverse array of complex N-containing molecules. The primary objective of the presentr eview is to bring the latest findings of TBN in terms of its applications in reactions (oxidation, diazotization, nitrosation, nitration, oximation, N-synthon, and miscellaneous reactions) into the limelight.F or simplicity and brevity,r eactions in each section are explained with the mechanism of formation and selected examples are given.Scheme1.Differential reactivity of TBN. 4455 MinireviewScheme4.Visible-light-promoted synthesis of selenide ethers.Scheme5.Proposed mechanism for visible-light-promoted synthesis of selenide ethers.Scheme6.TBN-mediated synthesis of selenide ethers.Scheme7.Metal-free synthesis of 4-carbonylquinolines.Scheme8.Proposed mechanism for synthesis of 4-carbonylquinolines.Scheme9.TBN-mediated demethylative borylation of methylarenes.Scheme10. Plausible mechanism for demethylative borylation of methylarenes.Scheme11. Trifluoromethylation of various aromatic amine substrates.Scheme12. Copper-catalyzed isoperfluoropropylation of anilines.Scheme13. Plausible mechanism for Cu-catalyzed isoperfluoropropylation of anilines.Scheme14. TBN-mediateddiazotizative allylation of aromatic amines.Scheme15. Oxidativecyanomethylationo fa lkenes via CÀHb ond activation.Scheme16. TBN-mediatedand Cu-catalyzedsynthesis of thioether.

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Section: Outlines Of the Reactions Involving Tbnmentioning

confidence: 99%

Section: Miscellaneousmentioning

confidence: 99%

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Dahiya

Sahoo

Alam

et al. 2019

Chemistry An Asian Journal

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“…Indole and its derivatives represent the most widely used and important heterocyclic compounds, which play a pivotal role in pharmaceutical and organic chemistry as a result of their unique structures and extensive biological and pharmacological properties. , In particular, indole-fused heteroacenes are widely presented in natural products, biologically active molecules, and functional materials. − Due to their significance, developing novel and efficient methods for the construction of indole-fused heteroacenes has drawn extensive attention from organic chemists. Over past decades, several approaches have been established for the synthesis of indole-fused heteroacenes, such as benzofuro-, benzothieno-, or indolo[3,2 -b ]indoles .…”

Section: Introductionmentioning

confidence: 99%

A Mild Two-Step Synthesis of Structurally Valuable Indole-Fused Derivatives

Chen

Jin

et al. 2022

J. Org. Chem.

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A mild two-step synthetic approach for the preparation of structurally valuable indolo[3′,2′:4,5]pyrrolo[3,2,1-kl]phenothiazines has been developed. In this work, cyclohexanone was used as the key bridge to connect the indole and phenothiazine frameworks to construct a structurally valuable indole-fused derivative. The present protocol achieved the cascade construction of multiple C–hetero bonds, affording a convenient approach access to hexacyclic-fused system that contained both indole and phenothiazine, two privileged skeletons.

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“…Such C-C triple bond reorganization has scarcely been reported in alkyne transformations. [23][24][25][26][27][28][29][30][31] The resultant quinolinone skeleton is prevalent in a large number of bioactive molecules and natural products. [32][33][34] Although various synthetic methods have been developed for their synthesis, [35][36][37][38][39] the present catalytic rearrangement offers a new step-and atom-economical route to access this framework from simple starting materials.…”

Section: Introductionmentioning

confidence: 99%

NHC-Boryl Radical Catalysis for Cycloisomerization With C–C Triple Bond Reorganization

et al. 2019

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Our present study unveils a new and efficient Nheterocyclic carbene (NHC)-boryl radical-catalyzed cycloisomerization of N-(2-ethynylaryl)arylamides. This catalytic process is triggered by the addition of an NHC-boryl radical to the alkynyl moiety, followed by a radical cascade comprising of an intramolecular cyclization, successive 1,5-and 1,2-aryl migrations, and the reorganization of a CC triple bond. Eventually, the catalytic cycle is achieved through a radical β-fragmentation reaction, from which the starting NHC-boryl radical is regenerated, and a structurally important quinolinone framework is assembled. A 13 C-labeling experiment was carried out to verify the CC triple bond reorganization, and the proposed catalytic pathway was supported further by density functional theory calculations. Our identification of NHC-boryl radical as a catalyst, as well as its mode of operation via radical addition/elimination mechanism, would stimulate the advancement of design of radical catalysis and the discovery of novel enantioselective radical-catalyzed processes.

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Direct Synthesis of Structurally Divergent Indole Alkaloids from Simple Chemicals

Cited by 21 publications

References 65 publications

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

A Mild Two-Step Synthesis of Structurally Valuable Indole-Fused Derivatives

NHC-Boryl Radical Catalysis for Cycloisomerization With C–C Triple Bond Reorganization

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