Indole frameworks <i>via</i> transition-metal-free annulation: a current perspective

Das, Suven

doi:10.1039/d3nj01488f

Cited by 9 publications

(2 citation statements)

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“…Various other organocatalytic and metal-free approaches have also been adopted accordingly. [46][47][48] However, during last few years, the use transition-metal as catalyst for obtaining this skeleton has achieved a milestone. [49][50][51][52] In this regard, copper has gained attention as an alternative to precious metals due to its low toxicity, high catalytic activity and cost-effectiveness.…”

Section: Introductionmentioning

confidence: 99%

“…The indole framework has been nurtured for nearly 150 years, and in general the purpose is realized by utilizing classical Fischer, [36] Bischler, [37] Reisert, [38] Madelung, [39] Bartoli, [40] Fukuyama, [41] Buchwald, [42] Gassman, [43] Hegedous, [44] Larock [45] indole synthesis. Various other organocatalytic and metal‐free approaches have also been adopted accordingly [46–48] . However, during last few years, the use transition‐metal as catalyst for obtaining this skeleton has achieved a milestone [49–52] .…”

Section: Introductionmentioning

confidence: 99%

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Copper–Catalyzed Construction of the Indole Core: Recent Advancements

Das,

Dutta

2024

ChemistrySelect

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Indoles are one of the most important heterocycles because of their widespread occurrence in bioactive natural products, synthetic drugs and organic materials. Therefore, development of efficient strategies for synthesizing functionalized indoles has been of great importance in organic synthesis. Copper, being a transition metal, meet the goal due to its low toxicity, high catalytic activity and cost‐effectiveness. In this review, we focus on last five year (2019–2023) advancement in copper‐catalyzed annulations for the construction of indole core involving various N‐containing substrates, which include anilines, o‐alkynylanilines, o‐aminophenylpropynols, o‐alkynylnitroarenes, o‐nitrochalcones, azidoalkynes, isonitriles, nitriles, enamines, imines, etc. Mechanistic aspects of the reactions have also been highlighted for better understanding of the reaction pathways.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Copper–Catalyzed Construction of the Indole Core: Recent Advancements

Das,

Dutta

2024

ChemistrySelect

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Base‐Promoted Structural Rearrangement of Ynamide and Simultaneous N‐Desulfonylation

Reddy Mutra,

Chandana,

Chang

et al. 2024

Adv Synth Catal

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The strategy of ynamide structural rearrangement is crucial in modern organic synthesis. The distinct carbon atoms in ynamides have different selectivity under various reaction conditions. Herein, we developed a base‐promoted regioselective and chemoselective cascade cyclization, ynamide N–Csp bond cleavage, selective intramolecular 1,3‐migration, and simultaneous N‐desulfonylation strategy for the synthesis of 2‐phenyl‐3‐(phenylethynyl)‐1H‐indole derivatives within a time of 15 min. We observed multiple bond breaking (‐N–Ts, and Csp2–Ts, Csp2–I/Csp2–SePh) from (E)‐3‐(1‐iodo‐2‐phenyl‐2‐tosylvinyl)‐2‐phenyl‐1‐tosyl‐indole/(E)‐2‐phenyl‐3‐(2‐phenyl‐1‐(phenylselanyl)‐2‐tosylvinyl)‐1‐tosyl‐indole derivatives to achieve 2‐phenyl‐3‐(phenylethynyl)‐1H‐indole in 15–60 min using our standard reaction conditions. A gram‐scale experiment and the postsynthetic transformation of the synthesized 2‐phenyl‐3‐(phenylethynyl)‐1H‐indole were conducted to exhibit the advantages of our synthetic methodology. The developed methodology has multiple advantages: a rapid reaction rate, regioselectivity and chemoselectivity, transition metal and acid oxidant free, preventing resource waste and a time‐consuming process in deprotecting steps, broad substrate scope, mild reaction condition, simple setup, ease of handle, gram‐scale experiment, and synthetic product transformations.

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Recent Advances in Domino Synthesis of Fused Polycyclic N‐Heterocycles Based on Intramolecular Alkyne Hydroamination under Copper Catalysis

Jin,

Shen,

2023

Chin. J. Chem.

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Comprehensive SummaryFused polycyclic N‐heterocycles are very important scaffolds in biomedicinal chemistry and materials science. Intramolecular alkyne hydroamination is a powerful method for the construction of N‐heterocycles. In the last two decades, copper‐catalyzed domino reactions based on intramolecular alkyne hydroamination has emerged as a robust strategy for assembling various fused polycyclic N‐heterocycles. Great progress has been achieved in this area. This short review covers the advances made in copper‐catalyzed domino synthesis of fused polycyclic N‐heterocycles based on the strategy from 2008 to 2023, and will hopefully serve as an inspiration towards the exploration of new copper‐catalyzed versions of the transformation. The domino transformations are introduced and discussed from five aspects according to the different key processes involved in these reactions.

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Indole frameworks via transition-metal-free annulation: a current perspective

Abstract: Indole structural motifs are ubiquitous in natural products, pharmaceuticals, agrochemicals and functional materials. The immense importance of indole moiety, especially in the field of drug discovery, has fuelled continued attention...

Cited by 9 publications

References 121 publications

Copper–Catalyzed Construction of the Indole Core: Recent Advancements

Copper–Catalyzed Construction of the Indole Core: Recent Advancements

Base‐Promoted Structural Rearrangement of Ynamide and Simultaneous N‐Desulfonylation

Recent Advances in Domino Synthesis of Fused Polycyclic N‐Heterocycles Based on Intramolecular Alkyne Hydroamination under Copper Catalysis

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