One-pot synthesis of polycyclic isoindolines using isoindole umpolung

Weintraub, Rachel A.; He, Wei; Wang, Xiang

doi:10.1016/j.tetlet.2020.152128

Cited by 3 publications

(4 citation statements)

References 16 publications

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“…A proposed mechanism of the reaction is outlined in Scheme 1c. Protonation of the isoindole intermediate should yield the isoindolium ion, 17 which is subsequently reduced to isoindoline by sodium triacetoxyborohydride (Na(OAc) 3 BH).…”

Section: Resultsmentioning

confidence: 99%

“…Recently, we reported an isoindole umpolung strategy for the polycyclic isoindoline synthesis. 17 Based on that work, 17 we envisioned that the reduction of the in situ generated isoindolium intermediate would yield the isoindoline (Scheme 1c). To test this hypothesis, we investigated a model reaction using ortho -bromomethyl benzaldehyde 1a with benzylamine 2a under different solvents, acids, and reductants at room temperature (Table 1).…”

Section: Resultsmentioning

confidence: 99%

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Practical synthesis of isoindolines yields potent colistin potentiators for multidrug-resistant Acinetobacter baumannii

Dutta,

Eyolfson,

Zhu

et al. 2024

Org. Biomol. Chem.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Practical synthesis of isoindolines yields potent colistin potentiators for multidrug-resistant Acinetobacter baumannii

Dutta,

Eyolfson,

Zhu

et al. 2024

Org. Biomol. Chem.

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“…In 2020, our research group reported a one-pot synthesis of polycyclic isoindolines (Scheme 4). 7 This reaction proceeds via an isoindole intermediate 28a that is formed in situ via a condensation reaction of a 2-(bromomethyl)benzaldehyde 27a with a -arylalkylamine 29a. This approach to isoindoles was based on previously reported literature, 9,55 such as the method reported by Sypchenko et al 55 in 2012 for the preparation of N-(2-aminophenyl)isoindoles 28b (Scheme 4) via the reaction of ortho-(bromomethyl)benzophenone 27c with 1,2-phenylenediamines 29b.…”

Section: Review Synthesismentioning

confidence: 99%

“…The one-pot synthesis of polycyclic isoindolines reported by our research group, which was introduced in Section 2.1.1, employed an isoindole umpolung strategy in which the nucleophilic in situ formed isoindoles 28a were protonated by TFA to convert them into the electrophilic isoindolium species 133 that subsequently underwent Pictet-Spengler-type cyclizations with the -arylethylamine moieties to give polycyclic isoindolines 134 in good yields (Scheme 33). 7 In the model reaction with 2-(bromomethyl)benzalde-hyde, tryptamine was used as the -arylethylamine reacting partner, as tryptamines are popular Pictet-Spengler substrates. Electron-rich and electron-poor tryptamines were well-tolerated, and only the latter reduced the yield, as they were worse nucleophiles in the Pictet-Spengler cyclization.…”

Section: Cyclization Reactionsmentioning

confidence: 99%

Recent Developments in Isoindole Chemistry

Wang¹,

Weintraub²

2022

Synthesis

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Isoindoles are highly reactive aromatic heterocycles that have a variety of important applications in areas such as medicine, analytical detection, and solar energy. Due to their highly reactive nature, isoindoles can be used to access their derivatives, which possess a diverse array of biological activities. However, their reactivity also makes isoindoles unstable and thus, difficult to prepare. Consequently, there has been a need for the development of novel methods that address some of the synthetic challenges and limitations, as well as reactions that utilize isoindoles to access potentially useful compounds. This review will give an overview of the novel reactions reported within the past decade (2012 to 2022) that involve 2H- and 1H-isoindoles and fused isoindoles as reactants, key intermediates, or products. This review is divided into two parts, with the first part focusing on the synthesis of isoindoles and the second part focusing on reactions of isoindoles. The scopes and limitations of the methods described therein will be discussed and the significance of their contributions to the literature will be highlighted. Similar reactions will also be compared.1 Introduction2 Synthesis of Isoindoles2.1 Synthesis of 2H-Isoindoles2.2 Synthesis of 1H-Isoindoles3 Reactions of Isoindoles3.1 Reactions of 2H-Isoindoles3.2 Reactions of 1H-Isoindoles4 Conclusions

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Palladium-Catalyzed α-Amino C–H Functionalization via Isomerization of α,β-Unsaturated Carbonyls

et al. 2022

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Palladium-catalyzed regioselective α-amino C–H functionalization via the isomerization of α,β-unsaturated carbonyls including esters, ketones, and amides has been established, providing an easy access to a wide array of tricyclic 1,2,3,4-tetrahydro-b-carbolines, azepinoindoles, 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles, 4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridines, 1,2,3,4-tetrahydropyrazino-[1,2-a]indoles, pyran-fused indoles, and tetrahydroisoquinolines in good to excellent yields. This transformation showed high regioselectivity, excellent functional group tolerance, and scalability. Moreover, this methodology was also employed as the key step for the total synthesis of desbromoarborescidines A, B, and C. Preliminary mechanistic studies revealed that the palladium catalyst not only formed [Pd–H] to promote the isomerization of α,β-unsaturated carbonyls but also played a role as a Lewis acid for the final protonation/cyclization.

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One-pot synthesis of polycyclic isoindolines using isoindole umpolung

Cited by 3 publications

References 16 publications

Practical synthesis of isoindolines yields potent colistin potentiators for multidrug-resistant Acinetobacter baumannii

Practical synthesis of isoindolines yields potent colistin potentiators for multidrug-resistant Acinetobacter baumannii

Recent Developments in Isoindole Chemistry

Palladium-Catalyzed α-Amino C–H Functionalization via Isomerization of α,β-Unsaturated Carbonyls

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