An unexpected transformation of 1,2-dialkyldiaziridines into N-{[acetyl(alkyl)amino]methyl}-N-(alken-1-yl)acetamide under the action of the parent ketene

Shevtsov, A. V.; Petukhova, V. Yu.; Strelenko, Yurii A.; Махова, Нина Н.

doi:10.1070/mc2005v015n01abeh001949

Cited by 21 publications

(9 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[12][13][14][15] Furthermore, diaziridines are prone to ring expansion reactions with electrophilic reagents (ketenes, isocyanates, isothiocyanates, and acylating reagents), which led to the development of new simple methods for the preparation of both known and previously unknown heterocyclic systems. 8,[16][17][18][19][20] And, finally, diaziridines have a high formation enthalpy as a result of the input both of the hydrazine fragment and three-member strained cycle and of low toxicity, which can be potentially useful for replacing hydrazine derivatives in rocket propellants. However some diaziridines had been absolutely or almost inaccessible (e.g.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of monocyclic diaziridines and their fused derivatives

Махова¹,

Petukhova²,

Кузнецов³

2008

Arkivoc

Self Cite

View full text Add to dashboard Cite

Diaziridines and their fused analogues have a wide-range potential as a test subjects for theoretical and practical application. This review covers our investigations focused on the development of optimal methods for the synthesis of monocyclic and fused diaziridine derivatives. Several approaches to the preparation of monocyclic diaziridine derivatives were developed: (1) a synthesis of 3,3-di-and 1,3,3-trialkylmono-and α,ω-bis(diaziridin-1-yl)alkanes from ketoxime O-sulfonates and ammonia, and primary aliphatic amines, respectively, as well as of practically previously inaccessible 3-monoalkyldiaziridines from ammonium salts of aldoxime O-sulfonic acids and ammonia (2) a synthesis of diaziridines from carbonyl compounds, primary aliphatic amines, and aminating reagents in water (or a water-MeOH mixture) at controlled pH of the medium, as well as from carbonyl compounds, amines and N-chloroalkylamines in aprotic solvents in the presence of K 2 CO 3, and (3) a synthesis of 1,2,3-trialkyldiaziridines from Nchloroalkylamines without carbonyl compounds in the presence of primary aliphatic amines at high pressure. As regards fused diaziridine derivatives, general and simple methods were developed to prepare four types of these structures: 1,5-diazabicyclo[3.1.0]hexanes, 1,6-diazabicyclo[4.1.0]heptanes, 1,3,5-triazabicyclo[3.1.0] hexanes, including the parent compound and 2,4-nonsubstituted structures, and 1,3,6-triazabicyclo[3.1.0]hexanes, the latter being previously unknown. The diastereomers have been isolated for 3,3′-bi-and 1,1′-alkylenebisdiaziridines. As a whole the investigations performed in our laboratory have resulted in the simple and general methods for preparing any kind of monocyclic and fused diaziridine derivatives that give high opportunities in the study of their chemical and stereochemical properties, and applications.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis of monocyclic diaziridines and their fused derivatives

Махова¹,

Petukhova²,

Кузнецов³

2008

Arkivoc

Self Cite

View full text Add to dashboard Cite

show abstract

“…For one example (the reac * On the occasion of the 75th anniversary of the foundation of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences. tion of 1,2 dialkyldiaziridines with benzoyl isothiocyanate), it was found that the use of the ionic liquids ( 6 ], where bmim is 1 butyl 3 methylimidazo lium) as the reaction medium results in the unexpected reaction pathway giving rise to 1,2,4,6 tetrazepane 5 thione derivatives. 7 In other solvents, these compounds also reacted with each other, but the reactions were very unselective and gave mixtures of several inseparable compounds.…”

mentioning

confidence: 99%

Insertion of carbon disulfide and the nitrile group into the diaziridine ring of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in ionic liquids catalyzed by BF3 · Et2O

2009

View full text Add to dashboard Cite

The present study revealed two new reactions resulting in the diaziridine ring expansion, viz., the insertion of the CS 2 molecule and the CN group of activated nitriles into the C-N bond of the diaziridine fragment of 6 aryl 1,5 diazabicyclo[3.1.0]hexanes. These reactions can be performed only in ionic liquids in the presence of BF 3 •Et 2 O as the catalyst. Based on these reactions, we developed simple one pot methods for the synthesis of 3 aryldihydro 5H pyrazolo[1,2 c][1,3,4]thiadiazole 1 thiones and 1 aryl 6,7 dihydro 1H,5H pyrazolo [1,2 a] [1,2,4]triazoles in high yields. Dipolar intermediates of new reactions, which are direct precursors of the final products, were detected by NMR methods. One of the intermediates was isolated and characterized. The reaction of 6 aryl 1,5 diazabicyclo[3.1.0]hexanes with benzoyl cyanide affords (2 benzoylpyrazolidin 1 yl)(aryl)acetonitriles.

show abstract

“…9), respectively. The reactions of 6 aryl 1,5 diaza bicyclo [ 6 ]) in the presence of a BF 3 •Et 2 O catalyst (Scheme 1) proceed through the formation of azomethine imine intermediates 7 with their subsequent cycloaddition to dipolarophiles, leading to 3 (aryl)dihydro 5H pyrazolo [1,2 c] [1,3,4]thiadiazole 1 thiones 5 and 1 aryl 6,7 di hydro 1H,5H pyrazolo[1,2 a] [1,2,4]triazoles 6. 7,8, 10 Earlier, 11 azomethine imines 7, generated similarly from 6 aryl 1,5 diazabicyclo[3.1.0]hexanes 2 in MeCN in the presence of Lewis acids (Et 2 O•BF 3 or In(OTf) 3 ) at 20 °C, were shown to undergo cycloaddition to N arylmaleimides, which are active dipolarophiles with the cis orientation of substituents at the double bond.…”

mentioning

confidence: 99%

Diaziridine ring expansion in 6-aryl-1,5-diazabicyclo[3.1.0]hexanes upon reactions with activated olefins in ionic liquids

et al. 2010

View full text Add to dashboard Cite

Reactions of 1,3 diphenylpropen 2 one and β nitrostyrenes with azomethine imines, generated from 6 aryl 1,5 diazabicyclo[3.1.0]hexanes on catalysis with Et 2 O•BF 3 in ionic liquids, were found to proceed with high regio and stereoselectivity to afford the products of the diaziridine ring expansion, viz., [3 aryl 2 phenyltetrahydro 1H,5H pyrazolo[1,2 a]pyrazol 1 yl](phenyl)methanones, 1,3 diaryl 2 nitrotetrahydro 1H,5H pyrazolo[1,2 a]pyrazoles and 5 aryl 6 (3 nitrophenyl) 2,3 dihydro 1H pyrazolo[1,2 a]pyrazolium tetrafluoroborates (hexafluorophosphates). The reactions discovered are new, more simple methods for the syn thesis of bicyclic structures.

show abstract

An unexpected transformation of 1,2-dialkyldiaziridines into N-{[acetyl(alkyl)amino]methyl}-N-(alken-1-yl)acetamide under the action of the parent ketene

Cited by 21 publications

References 5 publications

Synthesis of monocyclic diaziridines and their fused derivatives

Synthesis of monocyclic diaziridines and their fused derivatives

Insertion of carbon disulfide and the nitrile group into the diaziridine ring of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in ionic liquids catalyzed by BF3 · Et2O

Diaziridine ring expansion in 6-aryl-1,5-diazabicyclo[3.1.0]hexanes upon reactions with activated olefins in ionic liquids

Contact Info

Product

Resources

About