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Petukhova, V. Yu.; Kuznetzov, V. V.; Shevtsov, A. V.; Strelenko, Yu. À.; Махова, Нина Н.; Antipin, M. Yu.

doi:10.1023/a:1011352905841

Cited by 8 publications

(2 citation statements)

References 7 publications

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“…5,6 Using this approach we managed to synthesize the first representatives of 3,3′-bidiaziridines 17 from diimines 18 of glyoxal. 28 It was found that this approach could be used only for diimines 18 with branched alkyl substituents. Reactions of glyoxal with primary aliphatic amines containing normal aliphatic radicals did not terminate at the stage of diimines as they underwent further condensation or polymerization.…”

Section: 3′-bidiaziridines From Diimines Of Glyoxal and 12-bis(metmentioning

confidence: 99%

Synthesis of monocyclic diaziridines and their fused derivatives

Махова¹,

Petukhova²,

Кузнецов³

2008

Arkivoc

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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.

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Section: 3′-bidiaziridines From Diimines Of Glyoxal and 12-bis(metmentioning

confidence: 99%

Synthesis of monocyclic diaziridines and their fused derivatives

Махова¹,

Petukhova²,

Кузнецов³

2008

Arkivoc

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“…Even less reported in the literature is the synthesis of compounds similar to the biaziridines, namely bidiaziridines, interesting three-membered heterocyclic compounds containing two nitrogen atoms …”

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confidence: 99%

Stereoselective Synthesis and ROESY ¹H NMR Study of Bidiaziridines

et al. 2012

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The bisaziridination reaction of symmetric (E-s-trans-E)-α-diimines using ethyl nosyloxycarbamate as aminating agent yields symmetrically functionalized bidiaziridines, under mild conditions. The reactions take place with very high stereoselectivity giving only bidiaziridines with total retention of the starting α-diimine configuration, as determined by NMR measurements. Moreover, only a single pure diastereomer, derived from attack of the aza-anion on the opposite faces of conjugate system was obtained, starting from chiral substrates. ROESY analyses clearly show that all nitrogens have a stable pyramidal conformation, and the absolute configurations of new chiral centers were assigned.

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