Synthesis of acyloxy-2H-azirine and sulfonyloxy-2H-azirine derivatives via a one-pot reaction of β-enamino esters, PIDA and carboxylic acid or sulfonic acid

Tang, Pan; Wen, Long; Ma, Haojie; Yang, Yi; Jiang, Yan

doi:10.1039/d2ob00364c

Cited by 3 publications

(2 citation statements)

References 92 publications

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“…In 2022, Jiang and co-workers [20] reported PIDA mediated oxidative acyloxylation/azirination and sulfonyloxylation /azirination of β-enamino esters (Scheme 7). In this methodology, various acyloxy-2H-azirines and sulfonyloxy-2H-azirines were synthesized in moderate to good yields.…”

Section: Oxidation Of Enamine To 2h-azirinementioning

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: Oxidation Of Enamine To 2h-azirinementioning

confidence: 99%

2H‐Azirines: Recent Progress in Synthesis and Applications

Xu,

Zeng,

Luo

et al. 2024

Eur J Org Chem

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“…Because of their plethora of active electrophilic and nucleophilic sites, β-enamino esters are important intermediates in the synthesis of organic compounds. Jiang et al synthesized a range of functionalized acyloxy-2Hazirine and sulfonyloxy-2H-azirine derivatives in moderate to good yields (Scheme 46) [61]. This is the first time that oxidative sulfonyloxylation and azirination of β-enamino esters with PIDA and sulfonic acid have been used to access sulfonyloxy-2H-azirine.…”

Section: Construction Of Biologically Relevant Heterocycles 21 | Meta...mentioning

confidence: 99%

Applications of phenyliodine(III) diacetate in heterocyclic ringformations: An updatefrom 2015 to date

Alam

Hussien

Babu

et al. 2023

Journal of Heterocyclic Chem

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Diacetoxyiodobenzene (PhI(OAc)2), commonly referred to as DAIB or phenyliodine(III) diacetate (PIDA), is one of the most frequently used hypervalent iodines employed as an oxidizing agent in organic chemistry. In this review, PIDA is highlighted exclusively in relation to its applications in organic synthesis involving heterocyclic ring formations and is critically and in‐depth examined from the summer of 2015 to the present with a specific focus on the mechanistic pathway.

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Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Yoshimura,

Zhdankin

2024

Chem. Rev.

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Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. Hypervalent iodine reagents are commonly used in synthetically important halogenations, oxidations, aminations, heterocyclizations, and various oxidative functionalizations of organic substrates. Iodonium salts are important arylating reagents, while iodonium ylides and imides are excellent carbene and nitrene precursors. Various derivatives of benziodoxoles, such as azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, and alkenylbenziodoxoles have found wide application as group transfer reagents in the presence of transition metal catalysts, under metal-free conditions, or using photocatalysts under photoirradiation conditions. Development of hypervalent iodine catalytic systems and discovery of highly enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important recent achievement in the field of hypervalent iodine chemistry. Chemical transformations promoted by hypervalent iodine in many cases are unique and cannot be performed by using any other common, non-iodine-based reagent. This review covers literature published mainly in the last 7−8 years, between 2016 and 2024.

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Synthesis of acyloxy-2H-azirine and sulfonyloxy-2H-azirine derivatives via a one-pot reaction of β-enamino esters, PIDA and carboxylic acid or sulfonic acid

Cited by 3 publications

References 92 publications

2H‐Azirines: Recent Progress in Synthesis and Applications

2H‐Azirines: Recent Progress in Synthesis and Applications

Applications of phenyliodine(III) diacetate in heterocyclic ringformations: An updatefrom 2015 to date

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

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