On-Water Silver(I)-Catalyzed Cycloisomerization of Acetylenic Free Amines/Amides towards 7-Azaindole/Indole/Isoquinolone Derivatives

Sun, Hongpeng; Li, Xiao; Li, Wei; Xie, Qiong; Shao, Liming

doi:10.1055/s-0036-1589072

Cited by 15 publications

References 2 publications

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Reductive Cyclization of 2‐Nitro‐ and β‐Nitrostyrenes, 2‐Nitrobiphenyls, and 1‐Nitro‐1,3‐Dienes to Indoles, Carbazoles, and Pyrroles

Söderberg

Berkowitz

2022

Organic Reactions

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This chapter presents a comprehensive review of reductive cyclizations of 2‐nitro‐ and β‐nitrostyrenes, 2‐nitrobiphenyls, and 1‐nitro‐1,3‐dienes to furnish indoles, carbazoles, and pyrroles, respectively, as well as heteroatom analogs thereof. Two variations of the reductive cyclization are discussed: the Cadogan–Sundberg reaction, which is mediated by ternary phosphorus compounds, and the Watanabe–Cenini–Söderberg reaction, which employs a palladium catalyst in the presence of carbon monoxide. A few closely related reductive cyclizations are also presented, as are comparisons with other cyclizations that form the nitrogen–carbon bond of indoles and derivatives.

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Reductive Cyclization of 2‐Nitro‐ and β‐Nitrostyrenes, 2‐Nitrobiphenyls, and 1‐Nitro‐1,3‐Dienes to Indoles, Carbazoles, and Pyrroles

Söderberg

Berkowitz

2022

Organic Reactions

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2‐(Alkynyl)anilines and Derivatives — Versatile Reagents for Heterocyclic Synthesis

2022

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The transformations of 2‐alkynylanilines and their derivatives into heterocycles are surveyed. Depending on the substituents, catalysts, and reaction conditions, these substrates can be converted into indoles, quinolines, indolines, oxindoles, indoxiles, various polycyclic compounds, etc. This review aims to generalize and assess the patterns of reactivity, selectivity, and applicability of 2‐(alkynyl)anilines in heterocyclic chemistry. The review is divided into sections in accordance with the produced heterocycle. In summary, the title substrates are capable of cyclizing not only into five‐ and six‐membered rings, but also to produce seven‐ and even eight‐membered ring systems. The preparation of 2‐(alkynyl)anilines is not covered.

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Chemoselective Oxypalladation of (o‐Alkynylaryl)amide‐Triggered Site‐Selective C−H Annulation for Stereoselective Synthesis of Succinimide‐Fused Polycycles

Dattatri,

Babu Nanubolu,

Sridhar Reddy

2024

Adv Synth Catal

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We report herein a palladium‐catalyzed, site‐selective cyclative annulation of o‐alkynyl arylamides with maleimide for the stereoselective construction of succinimide‐incorporated benzoxazine derivatives. This operationally simple and modular protocol provides access to polycyclic frameworks. The other associated features are high functional group compatibility, gram‐scale synthetic potential, and downstream transformations. Control and labeling experiments were conducted to get insights into the mechanism.

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On-Water Silver(I)-Catalyzed Cycloisomerization of Acetylenic Free Amines/Amides towards 7-Azaindole/Indole/Isoquinolone Derivatives

Cited by 15 publications

References 2 publications

Reductive Cyclization of 2‐Nitro‐ and β‐Nitrostyrenes, 2‐Nitrobiphenyls, and 1‐Nitro‐1,3‐Dienes to Indoles, Carbazoles, and Pyrroles

Reductive Cyclization of 2‐Nitro‐ and β‐Nitrostyrenes, 2‐Nitrobiphenyls, and 1‐Nitro‐1,3‐Dienes to Indoles, Carbazoles, and Pyrroles

2‐(Alkynyl)anilines and Derivatives — Versatile Reagents for Heterocyclic Synthesis

Chemoselective Oxypalladation of (o‐Alkynylaryl)amide‐Triggered Site‐Selective C−H Annulation for Stereoselective Synthesis of Succinimide‐Fused Polycycles

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