Synthesis of Cyclohepta[<i>b</i>]indoles and Furo[3,4-<i>b</i>]carbazoles from Indoles, Tertiary Propargylic Alcohols, and Activated Alkynes

Yin, Haiting; Wu, Yinyin; Jiang, Yifan; Wang, Meifang; Wang, Shaoyin

doi:10.1021/acs.orglett.3c00885

Cited by 7 publications

(1 citation statement)

References 37 publications

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“…A robust metal-free three-component reaction has been developed leading to the preparation of cyclohepta [b]indole and furo [3,4-b]carbazole frameworks under acid catalysis in very mild conditions from indoles, tertiary propargylic alcohols, and activated alkynes. [57] The reaction proceeded satisfactorily tolerating a wide variety of substituents and providing the expected furo [3,4b]carbazole derivatives in modest to good yields.…”

Section: Thermal Cyclization Reactionsmentioning

confidence: 93%

Preparation of Carbazoles Involving 6π‐Electrocyclization, Photoredox‐, Electrochemical‐, and Thermal Cyclization Reactions: Mechanistic Insights

Romero,

Postigo,

Bonesi

2023

Chemistry A European J

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Carbazole is a heterocyclic motif that can be found in a diverse array of natural and unnatural products displaying a wide range of biological and physiological properties. Furthermore, this heterocycle is part of electronic materials like photoconducting polymers and organic optoelectronic materials owing to its excellent photophysical characteristics. Consequently, the development of synthetic strategies for carbazole scaffolds holds potential significance in biological and material fields. In this regard, a variety of preparation methods has been developed to exploit their efficient and distinct formation of new C−C and C‐heteroatom bonds under mild conditions and enabling broad substrate diversity and functional group tolerance. Therefore, this review focuses on the synthesis of a set of carbazole derivatives describing a variety of methodologies that involve direct irradiation, photosensitization, photoredox, electrochemical and thermal cyclization reactions.

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Section: Thermal Cyclization Reactionsmentioning

confidence: 93%

Preparation of Carbazoles Involving 6π‐Electrocyclization, Photoredox‐, Electrochemical‐, and Thermal Cyclization Reactions: Mechanistic Insights

Romero,

Postigo,

Bonesi

2023

Chemistry A European J

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Copper‐Catalyzed Radical‐Induced Annulation‐Halo(bi)cyanomethylation of Indole‐Tethered 1,6‐Enynes toward Pyrrolo[1,2‐a]indoles

Zuo,

Yuan,

Chen

et al. 2024

Adv Synth Catal

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A copper‐catalyzed radical‐induced annulation‐halocyanomethylation of indole‐linked 1,6‐enynes has been established using haloacetonitrile as radical precursors, enabling the synthesis of 21 cyanomethylated pyrrolo[1,2‐a]indoles with yields ranging from 42% to 81% and a Z/E ratio exceeding 19:1. Moreover, by adjusting the reaction temperature, a variation of the annulation‐bromobicyanomethylation process was achieved, resulting in the production of 12 bicyanomethylated pyrrolo[1,2‐a]indole isomers in the yields of 41‐68%. The stereoisomeric mixture of bicyanomethylated products could be purified to their pure configurations through recrystallization. The proposed reaction mechanism was formulated through a series of controlled experiments.

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Lewis Acid‐Catalyzed Tandem Annulation of Propargylic Alcohols with 2‐Allylphenols and Their Anti‐tumor Activities

Li,

Guo,

Liu

et al. 2024

Asian J Org Chem

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A novel bismuth(III) trifluoro‐methanesulfonate‐catalyzed and environmentally benign synthetic strategy for the construction of a wide range of structurally diverse, sophisticated [5,6,5]‐oxygen‐containing tricyclic frameworks with easy‐to handle propargylic alcohols and 2‐allylphenols as substrates in the presence of Bi(OTf)3 and AgOTf is described. This Lewis acid catalyzed [3 + 2] annulation protocol, which tolerates a great deal of functional groups, proceeds through a sequential Meyer‐Schuster rearrangement, nucleophilic substitution, 5‐exo‐trig cyclization, 5‐endo‐trig cyclization, and proton exchange sequences, affording a versatile approach for accessing oxygen‐containing tricyclic skeletons in moderate‐to‐excellent yields. In addition, most of the obtained compounds exhibited anti‐tumor activities against three types of human cancer cell lines in vitro, including Caco‐2 colon cancer cells, MCF‐7 breast cancer cells, and Hepg‐2 liver cancer cells.

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Synthesis of Cyclohepta[b]indoles and Furo[3,4-b]carbazoles from Indoles, Tertiary Propargylic Alcohols, and Activated Alkynes

Cited by 7 publications

References 37 publications

Preparation of Carbazoles Involving 6π‐Electrocyclization, Photoredox‐, Electrochemical‐, and Thermal Cyclization Reactions: Mechanistic Insights

Preparation of Carbazoles Involving 6π‐Electrocyclization, Photoredox‐, Electrochemical‐, and Thermal Cyclization Reactions: Mechanistic Insights

Copper‐Catalyzed Radical‐Induced Annulation‐Halo(bi)cyanomethylation of Indole‐Tethered 1,6‐Enynes toward Pyrrolo[1,2‐a]indoles

Lewis Acid‐Catalyzed Tandem Annulation of Propargylic Alcohols with 2‐Allylphenols and Their Anti‐tumor Activities

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