Reactions of Aziridines with Ring Expansion

“…Acylated aziridines can be rearranged to 2-oxazolines by the action of heat, nucleophiles, or acids. The rearrangement of thioacylaziridines proceeds analogously (7,8,(165)(166)(167)(168)(169)(170)(171).…”

Section: Reaction With Carbon Electrophilesmentioning

confidence: 99%

Imines, Cyclic

Scherr¹,

Steuerle²,

Fikentscher³

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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“…On the other hand, Aziridines are also well known as useful reagents for the synthesis of many categories of nitrogencontaining compounds, in particular N-heterocycles compounds such as oxazolines, thiazolidinones, thiazolidine thiones, and imidazolidinones [23].…”

mentioning

confidence: 99%

K5[PW11ZnO39].23H2O-catalyzed acylation/ring expansion of ketoaziridines in a single pot: a new regio- and stereo-selective route for the synthesis of oxazolines

2015

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and synthesis of the derivatives of serines as a antibiotics [13] synthesis of N-hydroxy-N-amino acids [14] and as starting material in the synthesis of the neurotrophic factor Lactacystin [15,16]. Moreover, various oxazolines with biological activity have been isolated from marine organisms [17,18].For many years, several synthetic methods have been described for the synthesis of oxazolines [19][20][21][22]. On the other hand, Aziridines are also well known as useful reagents for the synthesis of many categories of nitrogencontaining compounds, in particular N-heterocycles compounds such as oxazolines, thiazolidinones, thiazolidine thiones, and imidazolidinones [23].Among the synthetic applications of these compounds, the rearrangement of N-activated aziridines has become the object of attention only very recently [24]. Acyl aziridines could rearrange to oxazolines through a ring expansion reaction [25][26][27][28][29]. The ring expansion of N-acyl aziridines to oxazolines can be promoted by thermal, acidic, or nucleophilic conditions [30][31][32][33][34][35][36][37][38].However, catalytic examples for the synthesis of oxazolines are rare [39]. Here we report synthesis of N-acyl ketoaziridines from the corresponding ketoaziridines with acyl chlorides. Then N-acyl ketoaziridines in the presence of a nucleophilic and Lewis acids afforded oxazolines [40][41][42].Although a few methods have been described for the preparation of N-acyl aziridines none of them described direct synthesis of oxazolines from N-H aziridines with carboxylic acid .In continuation of our recent interest in the reaction of ketoaziridines [48] and success for using Polyoxometalates [49], herein, we report a one-pot regio-and stereo-selective synthesis of trans-4-benzoyloxazolines, catalyzed by the K 5 [PW 11 ZnO 39 ].23H 2 O catalytic system with moderate to good yields under mild conditions. Abstract A new and one-pot synthesis of oxazolines has been accomplished by K 5 [PW 11 ZnO 39 ].23H 2 O-catalyst acylation followed by C-N ring opening/C-O bond formation in NH ketoaziridines. This regio-and stereo-selective reaction presumably proceeds via a domino sequence resulting in the in situ generation of acyl aziridine which undergoes a ring expansion reaction via an initial C-N rupture of aziridine ring followed by ring closure to the oxazolines. The methodology provided novel one-pot procedure for the synthesis of trans-2,5-diaryl-4-aroyloxazolines.

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Aziridines

Deyrup¹

1983

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Reactions of Aziridines with Ring Expansion

Cited by 8 publications

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Imines, Cyclic

Imines, Cyclic

K5[PW11ZnO39].23H2O-catalyzed acylation/ring expansion of ketoaziridines in a single pot: a new regio- and stereo-selective route for the synthesis of oxazolines

Aziridines

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