A Domino Approach for the Synthesis of 4-Carboxamide Oxazolines from Azirines

Nikbakht, Ali; Mohammadi, Fariba; Mousavi, Mohammad Sadeq; Amiri, Kamran; Balalaie, Saeed; Röminger, Frank; Bijanzadeh, Hamid Reza

doi:10.1055/a-1558-7457

Cited by 5 publications

(5 citation statements)

References 7 publications

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“…The discovery of a regio‐ and diastereoselective ring‐expansion pathway of N ‐acylaziridines with a catalytic amount of InCl 3 was reported by Balalaie and co‐workers (Scheme 81b) [124] . Arylphenylazirines, isocyanides, and carboxylic acids could be reacted together via a domino Ugi Joullié/ring‐expansion reaction to afford 4‐carboxamide oxazolines in moderate to excellent yields.…”

Section: Reaction Of 2h‐azirinesmentioning

confidence: 94%

“…The discovery of a regio-and diastereoselective ringexpansion pathway of N-acylaziridines with a catalytic amount of InCl 3 was reported by Balalaie and co-workers (Scheme 81b). [124] Arylphenylazirines, isocyanides, and carboxylic acids could be reacted together via a domino Ugi Joullié/ringexpansion reaction to afford 4-carboxamide oxazolines in moderate to excellent yields. The stabilisation of catalytic intermediates allows its easy isolation and characterization, suggesting the reaction proceeds through the formation of Nacylaziridine intermediates via Ugi-Joullié adduction.…”

Section: The Addition Of C=n Of Azirinesmentioning

confidence: 99%

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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: 94%

Section: The Addition Of C=n Of 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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“…Kanizsai et al [ 43 ] first described the Lewis acid-promoted version of the Joullié–Ugi reaction using 2 H -azirine-2-carboxylates for the diastereoselective synthesis of N -acylaziridines-2-carboxamide derivatives ( Scheme 1 , Equation (3)). Furthermore, a domino JU-3CR/diastereoselective ring expansion reaction was applied in the preparation of oxazolines from 2-phenyl-2 H -azirines [ 44 ] ( Scheme 1 , Equation (4)).…”

Section: Introductionmentioning

confidence: 99%

“…). Furthermore, a domino JU-3CR/diastereoselective ring expansion reaction was applied in the preparation of oxazolines from 2-phenyl-2H-azirines [44] (Scheme 1, Equation ( 4)).…”

Section: Introductionmentioning

confidence: 99%

Diastereoselective ZnCl2-Mediated Joullié–Ugi Three-Component Reaction for the Preparation of Phosphorylated N-Acylaziridines from 2H-Azirines

Allende,

Olaizola,

Ochoa de Retana

et al. 2024

Molecules

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We disclose a direct approach to the diastereoselective synthesis of phosphorus substituted N-acylaziridines based on a one-pot ZnCl2-catalyzed Joullié–Ugi three-component reaction of phosphorylated 2H-azirines, carboxylic acids and isocyanides. Hence, this robust protocol offers rapid access to an array of N-acylaziridines in moderate-to-good yields and up to 98:2 dr for substrates over a wide scope. The relevance of this synthetic methodology was achieved via a gram-scale reaction and the further derivatization of the nitrogen-containing three-membered heterocycle. The diastereo- and regioselective ring expansion of the obtained N-acylaziridines to oxazole derivatives was accomplished in the presence of BF3·OEt2 as an efficient Lewid acid catalyst.

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“…A second family of amphiphilic reactants are isocyanides which can act as nucleophiles as well as electrophiles in organic synthesis . For instance, we reported a regio- and diastereoselective post-transformation domino approach to 4-carboxamide oxazolines from aryl-phenyl azirines, isocyanides, and carboxylic acids …”

Section: Introductionmentioning

confidence: 99%