Synthesis and Applications of Vinylaziridines and Ethynylaziridines

Ohno, Hiroaki

doi:10.1021/cr400543u

Cited by 192 publications

(62 citation statements)

References 331 publications

(253 reference statements)

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“…The synthesis and reactivity of aziridines have been reviewed from time to time. 2,3 Some review articles focusing on specific type of aziridines such as aziridine-2-carboxylates, 4 2-haloaziridines, 5 2-methyleneaziridines, 6 and 2-vinylaziridines 7,8 have been published. This review paper aims to describe recent applications (2008 to early 2017) of aziridines, whether activated or non-activated, in synthesis of other heterocyclic frameworks by aziridine ring expansion.…”

Section: Introductionmentioning

confidence: 99%

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Singh¹,

Sudheesh²,

Keroletswe³

2017

Arkivoc

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The inherent reactivity of the aziridine ring due to ring-strain makes it valuable building blocks for the synthesis of other heterocyclic motifs of biological relevance. Of particular significance is the generation of azomethine ylides from them and cycloaddition of ylides with alkenes, alkynes, and heterocumulenes. The ring undergoes opening followed by cyclization with a variety of reagents either in the presence of a catalyst or without any catalyst. This review article discusses the recent applications of aziridines in syntheses of four-to seven-membered heterocycles of biological relevance such as azetidines, 2

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Section: Introductionmentioning

confidence: 99%

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Singh¹,

Sudheesh²,

Keroletswe³

2017

Arkivoc

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“…[1][2][3][4][5] The relevant biological activity of these heterocycles, which are present in several natural compounds and antitumor/antimicrobial agents, [6][7][8][9][10] suggests their usage as precursors of important aza-compounds. [1][2][3][4][5] The relevant biological activity of these heterocycles, which are present in several natural compounds and antitumor/antimicrobial agents, [6][7][8][9][10] suggests their usage as precursors of important aza-compounds.…”

Section: Introductionmentioning

confidence: 99%

A mechanistic investigation of the ruthenium porphyrin catalysed aziridination of olefins by aryl azides

et al. 2015

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A mechanism for the aziridination of olefins by aryl azides (ArN3), promoted by ruthenium(ii) porphyrin complexes, is proposed on the basis of kinetic and theoretical studies. All the recorded data support the involvement of a mono-imido ruthenium complex as the active intermediate in the transfer of the nitrene moiety "ArN" to the olefin. The selectivity of the aziridination vs. the uncatalysed triazoline formation can be enhanced by fine-tuning the electronic features of the porphyrin ligand and the olefin/azide catalytic ratio. The DFT study highlights the importance of an accessible triplet ground state of the intermediate ruthenium mono-imido complex to allow the evolution of the aziridination process.

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“…The aziridine functionality is often responsible for the activity of biologically active species (such as antitumor compounds, antibiotics and enzyme inhibitors) and aziridine containing molecules [2] are also useful building blocks in the synthesis of fine chemicals and pharmaceuticals [3][4][5][6]. The striking chemical properties of aziridines are due to the energy associated to the strained threemembered ring [7], which renders them very active and versatile starting materials for the synthesis of several useful molecules such as amines, amino acids, β-lactams, polymers and α-amido ketones [8,9].…”

Section: Introductionmentioning

confidence: 99%

“…In view of their interesting chemical peculiarities and the scarcity of widespread procedures for their preparation [10], the scientific community is constantly interested in the development of new synthetic protocols which are more efficient than traditional methods such as cyclization of amino alcohols or the reaction between imines and diazo-containing compounds [9,11,12].…”

Section: Introductionmentioning

confidence: 99%

Aziridination of alkenes promoted by iron or ruthenium complexes

Damiano

Intrieri

Gallo

2018

Inorganica Chimica Acta

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Molecules containing an aziridine functional group are a versatile class of organic synthons due to the presence of a strained three member, which can be easily involved in ring-opening reactions and the aziridine functionality often show interesting pharmaceutical and/or biological behaviours. For these reasons, the scientific community is constantl y interested in developing efficient procedures to introduce an aziridine moiety into organic skeletons and the one-pot reaction of an alkene double bond with a nitrene [NR] source is a powerful synthetic strategy.Herein we describe the catalytic activity of iron or ruthenium complexes in promoting the reaction stated above by stressing the potential and limits of each synthetic protocol.

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Synthesis and Applications of Vinylaziridines and Ethynylaziridines

Cited by 192 publications

References 331 publications

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

A mechanistic investigation of the ruthenium porphyrin catalysed aziridination of olefins by aryl azides

Aziridination of alkenes promoted by iron or ruthenium complexes

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