CAN-mediated new, regioselective one-pot access to bicyclic cationic structures with 2,3-dihydro-1H-pyrazolo[1,2-a]pyrazol-4-ium core

Pleshchev, Mikhail I.; Gupta, Nikita V. Das; Кузнецов, В. В.; Fedyanin, Ivan V.; Качала, В. В.; Махова, Нина Н.

doi:10.1016/j.tet.2015.09.033

Cited by 26 publications

(9 citation statements)

References 46 publications

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“…treated 1,5‐diazabicyclo[3.1.0]hexanes 205 with ceric ammonium nitrate (CAN) to generate intermediate azomethine imines 206 , which underwent [3+2] cycloaddition with (2‐bromo‐2‐nitrovinyl)arenes 210 to deliver dihydro‐1 H ‐pyrazolo[1,2‐ a ]pyrazolium cations 211 and [Ce 3+ (NO 3 ) 6 ] 3− anion in high yield (Scheme 55). [99] …”

Section: Reactivities Of Diaziridines and Its Derivativesmentioning

confidence: 99%

Recent Advances in the Preparations and Synthetic Applications of Oxaziridines and Diaziridines

et al. 2021

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Oxaziridines and diaziridines have been used as versatile intermediates due to their high ring strain as well as the reactive CÀ O/N bond, for the synthesis of diverse range of nitrogen containing compounds. In the past few decades, numerous novel and handy methodologies on the preparations and utilizations of both the oxaziridines and diaziridines have been developed. In spite of few published reviews in the area (almost a decade back), the synthetic communities have made tremendous progress in their preparations and utilizations. This review has demonstrated the comprehensive advancement in the chemistry of oxaziridines and diaziridines for the last few years (almost a decade). 2.4. Oxaziridines from Ketimines 3. Reactivities of Oxaziridines 3.1. Oxygen Atom Transfer Reactions 3.2. Nitrogen Atom Transfer Reactions 3.3. Rearrangement Reactions of Oxaziridines 3.4. Cycloaddition Reactions 4. Synthesis of Diaziridines 4.1. Diaziridines from Imine Substrates 4.2. Bi-Diaziridines and Monocyclic Diaziridines using Nosyloxycarbamate 4.3. Alkenyl Diaziridines 4.4. Diaziridines using HOSA Reagent 4.5. N-Cyclopropyl Diaziridines 4.6. Synthesis of Diaziridines via Photocatalysis 5. Reactivities of Diaziridines and its Derivatives 6. Diaziridines as Intermediates 7. Conclusions

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Section: Reactivities Of Diaziridines and Its Derivativesmentioning

confidence: 99%

Recent Advances in the Preparations and Synthetic Applications of Oxaziridines and Diaziridines

et al. 2021

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“…19). CAN as the catalyst can trigger in situ diaziridine ring opening of bicyclic diaziridines or metathesis of azomethine imine, the occurrence of [3+2] cycloaddition of (2-bromo-2-nitrovinyl)arenes, followed by the aromatization of the formed pyrazolidine ring [101]. This metal catalysis of diaziridine ring opening approaches (Scheme 11 and Figure 19) provides the advantage of simplicity, and is a powerful tool for the synthesis of hydrazine bicyclic compounds.…”

Section: Metal Catalysis Of Diaziridines Ring Openingmentioning

confidence: 99%

“…The one-pot reaction of bicyclic diaziridines 152 and (2-bromo-2-nitrovinyl)arenes 153 resulting in bicyclic cationic 154 (2,3-dihydro-1H-pyrazolo[1,2-a]pyrazol-4-ium as cation and [Ce 3+ (NO 3 ) 6 ] 3− as anion) can only be conducted under the action of ceric ammonium nitrate (CAN) and MeCN (Figure19). CAN as the catalyst can trigger in situ diaziridine ring opening of bicyclic diaziridines or metathesis of azomethine imine, the occurrence of [3+2] cycloaddition of (2-bromo-2-nitrovinyl)arenes, followed by the aromatization of the formed pyrazolidine ring[101]. This metal catalysis of diaziridine ring opening approaches (Scheme 11 and Figure19) provides the advantage of simplicity, and is a powerful tool for the synthesis of hydrazine bicyclic compounds.…”

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confidence: 99%

New Trends in Diaziridine Formation and Transformation (a Review)

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This review focuses on diaziridine, a high strained three-membered heterocycle with two nitrogen atoms that plays an important role as one of the most important precursors of diazirine photoaffinity probes, as well as their formation and transformation. Recent research trends can be grouped into three categories, based on whether they have examined non-substituted, N-monosubstituted, or N,N-disubstituted diaziridines. The discussion expands on the conventional methods for recent applications, the current spread of studies, and the unconventional synthesis approaches arising over the last decade of publications.

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“…Diaziridines appeared to be suitable objects for studying of the stereochemistry of the nitrogen atom due to the high stability of the two stereogenic pyramidal nitrogens [21][22][23]. Strained diaziridine ring is inclined to ring-expansion reactions resulting in various ve-to-eight-membered monoand bicyclic heterocyclic structures [24][25][26][27][28][29][30]. These heterocycles possess high enthalpies of formation and though they contain hydrazine fragment are of low toxic compounds.…”

Section: Introductionmentioning

confidence: 99%

6,6′-Dimethyl-1,1′,5,5′-tetraaza-6,6′-bi(bicyclo[3.1.0]hexane): synthesis and investigation of molecular structure by quantum-chemical calculations, NMR spectroscopy and X-ray diffraction analysis

et al. 2021

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A new diaziridine derivative with two bicyclic diaziridine-containing moieties in one molecule, 6,6'dimethyl-1,1',5,5'-tetraaza-6,6'-bi(bicyclo[3.1.0]hexane) (BiDiMDAH), has been synthesized for the rst time. Its molecular structure has been investigated in the gas phase by means of quantum-chemical (QC) calculations, in CDCl 3 solution by 1D and 2D NMR spectroscopy and in the solid state by the X-ray diffraction (XRD) technique. It was found by QC calculations that BiDiMDAH molecule in a free state presents a single conformer of C 2 symmetry with trans orientation of the of the methyl groups about two carbons connecting diaziridine cycles. The 5-memebered rings in BiDiMDAH molecule has been found to be essentially planar. In order to explain conformational preferences of BiDiMDAH Natural Bond Orbitals (NBO) and Atoms in Molecules (AIM) analyses have been performed. According to the XRD data BiDiMDAH crystallizes in space group P2 1 /c with molecular structure similar to that obtained by the means of QC calculations. The data of NMR spectroscopy has revealed that only one conformer is present in CDCl 3 solution in agreement with the data of QC and XRD studies. The gaseous standard enthalpy of formation of BiDiMDAH has been estimated to be 443.8 ± 5.0 kJ/mol by means of G4 theory.

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CAN-mediated new, regioselective one-pot access to bicyclic cationic structures with 2,3-dihydro-1H-pyrazolo[1,2-a]pyrazol-4-ium core

Cited by 26 publications

References 46 publications

Recent Advances in the Preparations and Synthetic Applications of Oxaziridines and Diaziridines

Recent Advances in the Preparations and Synthetic Applications of Oxaziridines and Diaziridines

New Trends in Diaziridine Formation and Transformation (a Review)

6,6′-Dimethyl-1,1′,5,5′-tetraaza-6,6′-bi(bicyclo[3.1.0]hexane): synthesis and investigation of molecular structure by quantum-chemical calculations, NMR spectroscopy and X-ray diffraction analysis

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