Fe(NO3)3 as an efficient catalyst for regio- and stereo-controlled ring expansion of 1,2-diaroyl-3-arylaziridines

Samimi, Heshmat Allah; Shams, Zahra

doi:10.1007/s13738-013-0364-8

Cited by 7 publications

(8 citation statements)

References 37 publications

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“…Despite work reported on the synthesis of ketoaziridines, novel and widely applicable methods for the synthesis of them are still in demand. Throughout our earlier studies on the ketoaziridines [30][31][32][33][34][35][36][37], to further develop aziridination reaction, we have discovered a simple and stereo-selective one-pot method for the synthesis of ketoaziridines by the reaction of chalcones with 1-aminopyridinium iodide via in situ formation of N-N ylide. This method describes a novel method which for the first time utilizes 1-aminopyridinium iodide for the synthesis of aziridine in a one-pot reaction.…”

Section: Introductionmentioning

confidence: 99%

Aminopyridinium iodide as a NH transferring agent for the synthesis of 2-aroyl-3-aryl aziridines

Samimi

Momeni

2015

J IRAN CHEM SOC

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by bromination of the related α,β-unsaturated carbonyl compounds, followed with the reaction of ammonia solution [5][6][7][8][9][10].Another synthetic pathway for the synthesis of aziridinyl ketones involves formation of β-hydroxyamino derivatives followed by treatment with either metal alcoholates, or hydroxylamine hydrochloride and then potassium hydroxide [11][12][13][14]. It has been reported the interaction of unsaturated ketones with N-tosyliminoaryliodinanes in the presence of mono-valent copper complexes produces the related aziridinyl ketone [15,16].It was also reported that oximes could be converted into N-unsubstituted aziridines by treatment with Grignard reagents or by reduction with lithium aluminum hydride in certain cases [17].3,3-Pentamethyleneoxaziridine can transfer its NH group to electron-deficient olefins to give N-unsubstituted aziridines in low yields [17,18]. 2-ketoaziridine starting materials were also prepared using 1,4-addition of methoxyamine to α,β-unsaturated ketones followed by basepromoted ring closure [19]. Ylides are another kind of potential NH transfer agent. Free sulfimides HN = SR 2 , sulfur-nitrogen ylide [20][21][22][23][24], are used for the direct synthesis of N-unsubstituted aziridines. An one step synthesis of aziridine by the type addition off free sulfimide has been reported but yields are unsatisfactory and enaminoketones are obtained as major byproducts in moderate yields.On the other hand, an amineimide, as a type of nitrogennitrogen ylide, is an effective NH source for direct N-unsubstituted aziridination of electron-deficient olefins. Recently, a few method has been reported that tertiary amines such as N-methylmorpholin [25], 1,4-diazabicyclo[2.2.2]octane (DABCO) [26,27]. Quinine chiral tertiary amine [28] and Troger s base [29] can prepare amine imide which reacts with chalcone to give desire aziridinyl ketones (Scheme 1).Abstract A new approach for the synthesis of N-H ketoaziridines is described. 1-aminopyridinium iodide as a NH transferring agent provides a straightforward access to the 2-aroyl-3-arylaziridines from the corresponding 1,3-diarylprop-2-en-1-one. A possible general mechanism involving the N-N ylide is proposed.

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Section: Introductionmentioning

confidence: 99%

Aminopyridinium iodide as a NH transferring agent for the synthesis of 2-aroyl-3-aryl aziridines

Samimi

Momeni

2015

J IRAN CHEM SOC

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“…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.…”

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confidence: 99%

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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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“…[20][21][22][23][24][25][26][27] Previous reports have shown that replacement of the hydrogen of the N-H moiety with an electron-withdrawing substituent increases the susceptibility of N-H aziridines to ring-opening or ring-enlargement reactions. [28][29][30] So, our first aim was to synthesize N-Boc-substituted ketoaziridines as a precursor for preparation of the corresponding nitrogen-containing compounds via ring opening or ring enlargement.…”

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Synthesis of tert-Butyl 1,3-Diaryl-3-oxopropylcarbamates by a Regiocontrolled Reduction of Ketoaziridines

Samimi

Yamin²,

Saberi

2014

Synthesis

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A new, convenient approach for the reductive ring opening of N-H ketoaziridines is described. Treatment of N-H ketoaziridines with di-tert-butyl dicarbonate [(Boc) 2 O] in the presence of sodium iodide and nickel(II) chloride results in the corresponding tert-butyl 1,3-diaryl-3-oxopropylcarbamates by a regiocontrolled reaction. The structure of the regioisomeric product was confirmed by X-ray crystal structure analysis.

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Fe(NO3)3 as an efficient catalyst for regio- and stereo-controlled ring expansion of 1,2-diaroyl-3-arylaziridines

Cited by 7 publications

References 37 publications

Aminopyridinium iodide as a NH transferring agent for the synthesis of 2-aroyl-3-aryl aziridines

Aminopyridinium iodide as a NH transferring agent for the synthesis of 2-aroyl-3-aryl aziridines

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

Synthesis of tert-Butyl 1,3-Diaryl-3-oxopropylcarbamates by a Regiocontrolled Reduction of Ketoaziridines

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