An Assessment of Electrophilic N‐Transfer of Oxaziridine with Different 2‐, 3‐, and 4‐Carbon Donor–Acceptor Substrates to Furnish Diverse N‐Containing Heterocycles in a Single Step

Ghosh, Asit; Chawla, Vatan; Banerjee, Prabal

doi:10.1002/ejoc.201900589

Cited by 8 publications

(4 citation statements)

References 65 publications

(29 reference statements)

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“…The protocol delivered a number of valuable monocyclic as well as bicyclic heterocycles 99 with stereocenters and quaternary stereocenters using magnesium iodide as Lewis acid (Scheme 25). [53] The reactivity pattern of donor‐acceptor carbon substrates and oxaziridine in presence of MgI 2 was well described. The reaction pathway included the activation of donor‐acceptor carbon substrate and oxaziridine by the MgI 2 to generate the reactive intermediates 98I and 95I .…”

Section: Reactivities Of Oxaziridinesmentioning

confidence: 96%

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 Oxaziridinesmentioning

confidence: 96%

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

et al. 2021

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“…Oxaziridine 39 can be used simultaneously as oxidant and nitrogen source for oxidative nitrogen transfer alkene aziridinations in synthesis of 3-arylaziridine-2-carboxylates 1a1 , and diesters 1a8 as shown in the Scheme 40 [ 124 ]. The reaction was carried out under mild conditions in presence of MgI 2 .…”

Section: Aziridination Of Olefins (Path B)mentioning

confidence: 99%

“…Scheme 40. Oxaziridine-promoted oxidative aziridination [124]. N, N-dihalogene-p-toluenesulfonamides are reported as nitrogen sources for both catalytic [125,126] and non-catalytic [127] aziridinations of cinnamates, cinnamyl amides and chalcone type substrates 29a,c,d (Scheme 41).…”

Section: Hydroxylamines As Nitrogen Sourcesmentioning

confidence: 99%

3-Arylaziridine-2-carboxylic Acid Derivatives and (3-Arylaziridin-2-yl)ketones: The Aziridination Approaches

Strumfs

Uljanovs

Velikijs

et al. 2021

IJMS

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Aziridination reactions represent a powerful tool in aziridine synthesis. Significant progress has been achieved in this field in the last decades, whereas highly functionalized aziridines including 3-arylated aziridine-2-carbonyl compounds play an important role in both medical and synthetic chemistry. For the reasons listed, in the current review we have focused on the ways to obtain 3-arylated aziridines and on the recent advances (mainly since the year 2000) in the methodology of the synthesis of these compounds via aziridination.

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“…The nucleophilic attack of the anion of l to the N‐atom of intermediate li results in the formation of intermediate lii . The intermediate lii subsequently undergoes cyclization to form the N‐transferred product 179 (Scheme ) …”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Donor–Acceptor Cyclopropanes as an Expedient Building Block Towards the Construction of Nitrogen‐Containing Molecules: An Update

et al. 2020

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Nitrogen‐containing molecules are the key structural constituent of many pharmaceutical compounds that play a pivotal role in drug development. Owing to their multifaceted medicinal importance, several synthetic approaches have been delineated in the recent past for their construction. Over the past few decades the augmented use of donor–acceptor cyclopropanes (DACs) as three‐carbon synthetic equivalents, despite their ring strain, for the construction of innumerable hetero‐ and carbocycles of pharmaceutical importance has raised the interest of synthetic chemists to this topic. Owing to their zwitterionic nature due to the vicinal disposition of donor and acceptor groups, they have been frequently used in ring‐opening reactions, cycloadditions, and rearrangements. This review is mainly focused on assorted reactions of DACs with various nitrogen‐containing dipolarophiles like imines, azides, cyanates, isothiocyanates, nitrosocarbonyls, hydrazines, diaziridines, triazinanes, diazenes, etc. towards the synthesis of nitrogen‐containing molecules of pharmaceutical and industrial importance. This review is in continuation of our review published in the Israel Journal of Chemistry in April 2016, and includes the literature from April 2016 to May 2019.

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An Assessment of Electrophilic N‐Transfer of Oxaziridine with Different 2‐, 3‐, and 4‐Carbon Donor–Acceptor Substrates to Furnish Diverse N‐Containing Heterocycles in a Single Step

Cited by 8 publications

References 65 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

3-Arylaziridine-2-carboxylic Acid Derivatives and (3-Arylaziridin-2-yl)ketones: The Aziridination Approaches

Donor–Acceptor Cyclopropanes as an Expedient Building Block Towards the Construction of Nitrogen‐Containing Molecules: An Update

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