Nucleophilic ring opening reactions of aziridines

Akhtar, Rabia; Naqvi, Syed Ali Raza; Zahoor, Ameer Fawad; Saleem, Sameera

doi:10.1007/s11030-018-9829-0

Cited by 66 publications

(41 citation statements)

References 126 publications

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“…[25 -33] Our group is also involved in this field and reported the synthesis Supporting information for this article is available on the WWW under https://doi.org/10.1002/hlca.201900199 1 For a review on aziridine ring opening reactions with different nucleophiles see ref. [10]. of racemic and chiral aziridine-2-phosphonates by modified Gabriel -Cromwell reaction and the results of their antibacterial activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Functionalized Novel α‐Amino‐β‐alkoxyphosphonates through Regioselective Ring Opening of Aziridine‐2‐phosphonates

Polat-Çakır

Beksultanova

Doğan

2019

Helvetica Chimica Acta

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Aziridines are highly useful compounds as building blocks for the synthesis of important organic compounds. Amino acid synthesis by aziridine ring opening reaction is a good example to the use of aziridines. Although this reaction is studied by many groups, the synthesis of amino phosphonic acids is less explored. In this study, we have carried out the ring opening reaction of aziridinyl phosphonates with a variety of alcohols including the more functional propargylic and allylic alcohols. These reactions provided functionalized α‐amino‐β‐alkoxyphosphonates in 40–91 % yield.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Functionalized Novel α‐Amino‐β‐alkoxyphosphonates through Regioselective Ring Opening of Aziridine‐2‐phosphonates

Polat-Çakır

Beksultanova

Doğan

2019

Helvetica Chimica Acta

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“…104−106 • Ring-opening reactions, which represent very versatile methods for polymer transformations. The nucleophilic ring opening of strained heterocycles, such as epoxides, 107,108 aziridines, 109,110 and azlactones, 111,112 enables the introduction of desired heteroatoms on the polymer backbone. • Multicomponent reactions (MCRs), including isocyanide-based, non-isocyanide-based and organometalliccatalyzed reactions.…”

Section: Acs Applied Nano Materialsmentioning

confidence: 99%

Nanogel Functionalization: A Versatile Approach To Meet the Challenges of Drug and Gene Delivery

Mauri

Perale

Rossi

2018

ACS Appl. Nano Mater.

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The design of nanostructures carrying therapeutic molecules represents the new frontier in the biological and medical fields. In particular, researchers have identified nanogels as promising tools in response to the critical issues of intracellular delivery: because of their peculiar properties, including swelling behavior, nanogels are able to cross the cellular membrane (clathrin-mediated endocytosis, caveolin-mediated endocytosis, phagocytosis, and macropinocytosis) and release their cargo in the cytosol, avoiding the activation of immune responses. However, only the combination of different starting polymers is not enough for the development of selective and targeted nanocarriers. The orthogonal functionalization of polymer chains with different chemical groups allows grafting of specific moieties and conjugating biomolecules, such as peptides, proteins, and growth factors, to give rise to nanogels that are not only more attractive but also more efficient in drug and gene delivery, with the ability to reach specific sites and trigger selective therapies. Moreover, the functionalization techniques offer the opportunity to improve load protection until the desired area is reached and synthesize nanosystems that are sensitive to biological stimuli. This review discusses the key role of nanogel functionalization to design promising nanonetworks for drug and gene delivery, highlighting how modification of the polymer meets the challenges of biomolecule transport, and summarizes the most recent results recorded in these fields. A brief mention is also accorded to the functionalization approach to produce detectable nanogels in vitro and in vivo, ensuring their traceability over time.

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“…The ring opening of heterocyclic 3-membered rings is an established and versatile strategy in the synthetic chemists' toolbox for the generation of new stereogenic sites in complex molecules and has been applied in the nucleophilic ring opening of chiral oxiranes [1][2][3] and aziridines [4][5][6] (Scheme 1) in the syntheses of natural products, medicinal drugs and material structures. The evolution of this ring-opening methodology to incorporate other heterocycles, for example, phosphorus atoms to produce phosphiranes, is hampered by the apparent instability of these systems.…”

Section: Introductionmentioning

confidence: 99%

Predicting phosphirane air stability using density functional theory

Gaston

McCosker

et al. 2020

J of Physical Organic Chem

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Phosphorus 3‐membered heterocycles, phosphiranes, provide an interesting synthetic scaffold with a potentially diverse range of reactions that are currently underexplored. This is in part due to their difficulty in synthesis, with many products and intermediates containing low air stability. With the application and extension of a density functional theory (DFT) model to phosphiranes by calculation at the UB3LYP/6‐31G(d) level of their radical cation singly occupied molecular orbital (SOMO), a correlation between calculated and relative experimental air stability has been demonstrated. The model also accounts for the stability of many synthesised substituted and unsubstituted phosphiranes and has allowed new synthetic targets to be identified, in particular, 1‐(2,4,6‐tri‐tert‐butoxyphenyl)phosphirane exhibited high theoretical air stability. Because of the simplicity and efficiency of the model, its application enables phosphiranes to be screened for high bench stability, providing accessibility for their use in synthetic chemistry, in turn, realising the potential for incorporation of phosphiranes into complex synthetic strategies.

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Nucleophilic ring opening reactions of aziridines

Cited by 66 publications

References 126 publications

Synthesis of Functionalized Novel α‐Amino‐β‐alkoxyphosphonates through Regioselective Ring Opening of Aziridine‐2‐phosphonates

Synthesis of Functionalized Novel α‐Amino‐β‐alkoxyphosphonates through Regioselective Ring Opening of Aziridine‐2‐phosphonates

Nanogel Functionalization: A Versatile Approach To Meet the Challenges of Drug and Gene Delivery

Predicting phosphirane air stability using density functional theory

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