Visible Light Organo‐Photocatalytic Synthesis of 3‐Imidazolines

Mishra, Poornima; Shruti, Ipsha; Kant, Ravi; Thakur, Tejender S.; Kumar, Akhilesh; Rastogi, Namrata

doi:10.1002/ejoc.202201079

Cited by 4 publications

(2 citation statements)

References 71 publications

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“…Rastogi and co‐workers [73] observed the formation of tetrasubstituted 3‐imidazolines in the organic dye catalyzed reaction of 2H ‐azirines and N ‐tosyl benzylidene imines (Scheme 46). A separable mixture of cis and trans isomers can be isolated by silica gel column chromatography.…”

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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“…12 Although there are many reported cyclizations of 2 H -azirines that proceed via light-induced pathways, light-induced diastereoselective transformations of 2 H -azirines remain unexplored; there are few examples of a diastereoselective transformation that proceeds via ring opening of 2 H -azirines under light irradiation. 13 The pyrrolo-[3,4- c ]pyrrole-1,3-dione moiety is an attractive scaffold that can be found in pharmacologically relevant compounds showing several different biological activities (Fig. 1), 14 such as acetylcholinesterase inhibition ( A ), thrombin Inhibition ( B ) and 3CL-protease of SARS-CoV-2 inhibition ( C ).…”

Section: Introductionmentioning

confidence: 99%

Visible light-promoted synthesis of 4,6a-dihydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dionesvia[3+2] cycloaddition reaction of 2H-azirines with maleimides

et al. 2023

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Organophotoredox‐mediated Formal [3+2]‐Cycloaddition of 2H‐Azirines with Aryldiazonium Salts: Direct Access to Trisubstituted 1,2,4‐Triazoles

Mishra

Kumar

Srivastava

et al. 2023

Chemistry An Asian Journal

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The present work documents an organophotoredox-mediated formal [3 + 2]-cycloaddition of 2H-azirines with aryl diazonium tetrafluoroborate salts to furnish 1,3,5trisubstituted 1,2,4-triazoles. The reaction furnishes a regioisomeric mixture of 1,2,4-triazoles in case of unsymmetrically substituted azirines. It is noteworthy that aryl radical generation from diazonium salt under visible light photoredox conditions could be successfully avoided by carefully selecting the reaction conditions.

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Visible Light Organo‐Photocatalytic Synthesis of 3‐Imidazolines

Cited by 4 publications

References 71 publications

2H‐Azirines: Recent Progress in Synthesis and Applications

2H‐Azirines: Recent Progress in Synthesis and Applications

Visible light-promoted synthesis of 4,6a-dihydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dionesvia[3+2] cycloaddition reaction of 2H-azirines with maleimides

Organophotoredox‐mediated Formal [3+2]‐Cycloaddition of 2H‐Azirines with Aryldiazonium Salts: Direct Access to Trisubstituted 1,2,4‐Triazoles

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