Regio- and stereo-controlled isomerization of 1,2-diaroyl-3-aryl aziridines to the corresponding N-((Z)-1-oxo-1,3-diphenylprop-2-en-2-yl) benzamide

Samimi, Heshmat Allah; Yamin, Bohari Mohd.; Soltani, Marzieh

doi:10.1007/s13738-014-0416-8

Cited by 2 publications

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“…trans-2-Aroyl-3-arylaziridines 80 were converted into N-[(Z)-1-aroyl-2-arylvinyl]benzamides 83 by a two-step procedure (Scheme 20). 30 The key transformation is the regio-and stereocontrolled isomerization of the intermediate N-acylaziridines 81 via formation of 82 upon treatment with N,N′diethylthiourea. The nature of substituents on aziridine carbon atoms governs regioselectivity of the addition of the thiourea.…”

Section: Scheme 19mentioning

confidence: 99%

Recent Advances in the Chemistry of 2-Acylaziridines

Pankova

Кузнецов

2017

Synthesis

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This review highlights recent achievements in the transformations of 2-acylaziridines toward the synthesis of cyclic and acyclic nitrogen-containing compounds. The influence of a carbonyl group on reaction selectivity is discussed.1 Introduction2 Reactions via C–C Bond Cleavage3 Reactions via C–N Bond Cleavage3.1 Reactions Starting with the Aziridine Ring Opening3.2 Reactions Starting at the Carbonyl Group4 Conclusion

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Section: Scheme 19mentioning

confidence: 99%

Recent Advances in the Chemistry of 2-Acylaziridines

Pankova

Кузнецов

2017

Synthesis

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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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Regio- and stereo-controlled isomerization of 1,2-diaroyl-3-aryl aziridines to the corresponding N-((Z)-1-oxo-1,3-diphenylprop-2-en-2-yl) benzamide

Cited by 2 publications

References 50 publications

Recent Advances in the Chemistry of 2-Acylaziridines

Recent Advances in the Chemistry of 2-Acylaziridines

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

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