Cascade Reaction of 2-Naphthols and Azirines: One-Pot Synthesis of C-3 Naphthol-Substituted Benzo[<i>e</i>]indoles

Xie, Fang; Sun, Yi‐Feng; Song, Hanghang; Zhao, Jie; Zhang, Zengpeng; Duan, Yue; Chen, Rao

doi:10.1021/acs.joc.1c02164

Cited by 13 publications

(4 citation statements)

References 77 publications

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“…Xie and co‐workers [59] reported the rapid assembly of π‐expanded C‐3 naphthol‐substituted benzo[e]indoles (Scheme 34). When copper(I) acetate (10 mol%) and Cs 2 CO 3 were employed in refluxing DCE in the presence of PIDA under nitrogen atmosphere, smooth conversion to naphthol/benzo[e]‐indole biaryls was observed.…”

Section: Reaction Of 2h‐azirinesmentioning

confidence: 99%

2H‐Azirines: Recent Progress in Synthesis and Applications

Xu,

Zeng,

Luo

et al. 2024

Eur J Org Chem

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2H‐arizines are important three‐membered heterocycles in organic chemistry. Recently, many advances in the synthesis and functionalization of 2H‐arizines have been reported. Neber rearrangement, isomerization of isoxazole, oxidation of enamine, C–H bond activation, decomposition of vinyl azide, functionalization of alkyne, and multi‐step synthesis have been developed for the efficient assembly of 2H‐azirines. As versatile and highly strained three‐membered unsaturated heterocycles, 2H‐azirines can be used as distinctive building blocks towards significant functional groups, and have attracted extensive attention for the fabrication of numerous heterocycles. Recent studies have focused on [3+n] ring‐expansion reactions, nucleophilic addition of C=N double bond or continuous nucleophilic addition followed by cyclization, ring‐opening of 2H‐azirines to acyclic compounds, and substitution of sp3‐C‐H of 2H‐azirines. One of the most critical challenges is seeking for a selective opening of the specific three bonds of the strained azirine circle, some of what can be achieved on the basis of metal catalyst, photocatalysis, or combination of metal catalyst and photocatalysis. In this review, recent advances involving the synthesis and reactivity of 2H‐arizines accompanied with challenges and breakthroughs are summarized. The review mainly covers the period from 2019 to 2023.

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Section: Reaction Of 2h‐azirinesmentioning

confidence: 99%

2H‐Azirines: Recent Progress in Synthesis and Applications

Xu,

Zeng,

Luo

et al. 2024

Eur J Org Chem

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“…Subsequently, a second molecule of 2-naphthol reacts via cross-dehydrogenative coupling to produce cyclized naphthol-substituted benzo[e]indole derivatives (Scheme 101). 120…”

Section: Tandem Copper-catalyzed Cyclization Involving Nucleophilic A...mentioning

confidence: 99%

Recent advances in the tandem copper-catalyzed Ullmann–GoldbergN-arylation–cyclization strategies

2022

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“…For example, traditional approaches like (i) transition-metal-catalyzed or base-promoted arylation, − (ii) alkylation or dimerization, and (iii) transition-metal-catalyzed intermolecular oxidative annulation − often rely on multistep reactions and complex reaction conditions, leading to low overall yields and increased production costs. In contrast, the intramolecular C–N construction techniques, such as (iv) transition-metal-catalyzed cyclization , and (v) intramolecular amination/oxygenation − offer more efficient and sustainable routes to these compounds. However, challenges remain in terms of scalability, selectivity, and environmental impact, highlighting the need for continued innovation in synthetic methodologies for indole and benzofuran derivatives.…”

Section: Introductionmentioning

confidence: 99%

Construction of 2-Substituted-3-aryl Benzofurans and Indoles through an Acid-Catalyzed Cascade Intramolecular Friedel-Crafts Reaction/Rearrangement/Aromatization Process

Liu,

Cheng

et al. 2024

J. Org. Chem.

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We present here a new method for the synthesis of 2-substituted-3-aryl benzoheterocycles through a more challenging constrained [1,5]-type Friedel–Crafts reaction/rearrangement and aromatization process. By using the readily available 2-aryoxy-1,3-indandiones and 2-arylamino-1,3-indandiones, a range of 2-substituted-3-aryl benzofurans and indoles were prepared in good to excellent yields (yields up to 86%) under the catalysis of CF3SO3H or Sm(OTf)3. Compared with previous methods for constructing similar structures, this approach offers several advantages, including the use of easily accessible starting materials, mild reaction conditions, high yield, excellent regio- and diastereoselectivity, and a broad substrate scope.

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Cascade Reaction of 2-Naphthols and Azirines: One-Pot Synthesis of C-3 Naphthol-Substituted Benzo[e]indoles

Cited by 13 publications

References 77 publications

2H‐Azirines: Recent Progress in Synthesis and Applications

2H‐Azirines: Recent Progress in Synthesis and Applications

Recent advances in the tandem copper-catalyzed Ullmann–GoldbergN-arylation–cyclization strategies

Construction of 2-Substituted-3-aryl Benzofurans and Indoles through an Acid-Catalyzed Cascade Intramolecular Friedel-Crafts Reaction/Rearrangement/Aromatization Process

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