Synthesis and transformations of 1,3,5-triazabicyclo[3.1.0]hexanes

Махова, Нина Н.; Mikhailyuk, A. N.; Bova, A. E.; Chabina, T. V.; Khmel'nitskii, L. I.

doi:10.1007/bf00698884

Cited by 5 publications

(4 citation statements)

References 8 publications

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“…The best conditions for the synthesis of compounds 44b,c proved to be condensation of diaziridines 13a,b with NH 3 and CH 2 O in water with subsequent twofold treatment with K 2 CO 3 , extraction of the resulting organic layer into the aprotic organic solvent, and exposure to a basic dehydrating reagent such as K 2 CO 3 or BaO (Scheme 16). 56,57 The yields of compounds 44b,c under these conditions were 85-91%, and the yield of by-55 did not exceed 5%. Presumably, the first step of this reaction in water is kinetically controlled α-aminomethylation of diaziridines 13a,b to give an intermediate of type 57, which unless it is diverted, is in the equilibrium with the starting materials and gradually decomposes giving 55 as thermodynamic the product of reaction.…”

Section: Synthesis Of Fused Diaziridine Derivativesmentioning

confidence: 83%

“…However when NH 3 was replaced by primary aliphatic amines or amino acids the reaction was unambiguously in giving 3-substituted 1,3,5-triazabicyclo[3.1.0]hexanes 44d-n. 3-Methyldiaziridine 13a also was entered this reaction successfully (Scheme 17). 57,58 . The reaction of diaziridine 61b with aromatic and heteroaromatic aldehydes proceeded diastereoselectively to form a mixture of two racemates 1R*,2R*,5R*,6R* 64a-d and 1R*,2S*,5R*,6R* 65a-d in a ratio of (3-20) : 1.…”

Section: Synthesis Of Fused Diaziridine Derivativesmentioning

confidence: 99%

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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: Synthesis Of Fused Diaziridine Derivativesmentioning

confidence: 83%

Section: Synthesis Of Fused Diaziridine Derivativesmentioning

confidence: 99%

Synthesis of monocyclic diaziridines and their fused derivatives

Махова¹,

Petukhova²,

Кузнецов³

2008

Arkivoc

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“…Previously, nitro groups were introduced at the diaziridine ring only in combination with other substituents (structures I and II , Scheme ). Compound I was synthesized by nitration of 3-trimethylsilyl-1,3,5-triazabicyclo[3.1.0]hexanes with N 2 O 5 in aprotic medium . N-Alkylation of 3-methyldiaziridine with 2-nitrazapropyl bromide was used for the synthesis of compound II …”

Section: Introductionmentioning

confidence: 99%

“…Compound I was synthesized by nitration of 3-trimethylsilyl-1,3,5triazabicyclo[3.1.0]hexanes with N 2 O 5 in aprotic medium. 37 N-Alkylation of 3-methyldiaziridine with 2-nitrazapropyl bromide was used for the synthesis of compound II. 38 The abovementioned method for nitration of N-trimethylsilyl derivatives was previously used for the synthesis of both N-nitroaziridines 39,40 and N-nitrohydrazines.…”

Section: Introductionmentioning

confidence: 99%

Nitrodiaziridines: Unattainable yet, but Desired Energetic Materials

et al. 2021

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Using quantum chemical methods and the original technique based on atom–atom potential methods, the molecular and crystal structure simulation of all possible structural forms of nitrodiaziridines were carried out. The possible pathways of thermal decomposition of nitrodiaziridines were modeled, and the most stable forms were identified. Thermodynamic stability, physicochemical characteristics, and detonation properties were also estimated. The obtained results enable a huge potential of the nitrodiaziridine-based compounds as high-energy materials for a variety of applications.

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