A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides

Teterina, Polina S.; Efremova, Mariia M.; Sirotkina, Ekaterina V.; Novikov, Alexander S.; Khoroshilova, Olesya V.; Molchanov, A. P.

doi:10.1016/j.tetlet.2019.151063

Cited by 12 publications

(8 citation statements)

References 65 publications

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“…Xcalibur, Eos diffractometer was used for X-ray analysis. ( E )-methyl 2-(2-oxoindolin-3-ylidene)acetates 1a,b and nitrones 2a–d , 5a–c were prepared using known procedures [ 61 , 64 , 65 ].…”

Section: Methodsmentioning

confidence: 99%

“…Moreover, due to the ease of the N–O bond cleavage in the isoxazolidine ring under reductive conditions, these compounds can be used for the synthesis of 1,3-aminoalcohols [ 52 , 53 , 54 ], biologically valuable β-lactams [ 55 , 56 , 57 , 58 , 59 ], and amino acids [ 60 ]. The presence of additional functional groups in the isoxazolidine ring significantly expands the possibilities of using these substrates in organic synthesis [ 61 , 62 ].…”

Section: Introductionmentioning

confidence: 99%

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Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines

Kartsev

Efremova

Molchanov

et al. 2022

IJMS

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The 1,3-dipolar cycloaddition of 2-(2-oxoindoline-3-ylidene)acetates with functionalized aldo- and ketonitrones proceeds with good selectivity to provide new highly functionalized 5-spiroisoxazolidines. A characteristic feature of these reactions is reversibility that allows for the control of the diastereoselectivity of cycloaddition. The reduction of obtained adducts using zinc powder in acetic acid leads to 1,3-aminoalcohols or spirolactones. For a number of the spiro compounds obtained, anticancer activity was found.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines

Kartsev

Efremova

Molchanov

et al. 2022

IJMS

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“…On similar lines, a dipolar cycloaddition describes the reaction between N ‐aryl itaconimides 1 and various nitrones 18 a for the rapid synthesis of isoxazolidines 18 b (Scheme 18). [41] While its notifying ability to construct complex isoxazolidines, in most of the cases a mixture of separable diastereomers were obtained.…”

Section: Synthetic Applicationmentioning

confidence: 99%

A Review on the Synthesis and Applications of α‐Alkylidene Succinimides

Nagaraju

Nanda

2022

Asian J Org Chem

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The widespread biological activity and manifestation of multiple reactive centers in itaconimides/α‐alkylidene succinimides have made them as one of the valuable synthetic targets. In this domain, various strategies have been developed to portray the proficiency of these N‐bearing heterocycles. The current review summarizes the biological activity, synthesis, and use of itaconimides/α‐alkylidene succinimide in numerous useful transformations under many reacting environments.

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“…An interesting case of a 32CA reaction involving N-aryl-C-carbamoylnitrone (nitrone 1) and N-arylitaconimide (ethylene 2) was described recently by Teterina et al [26] In this 32CA reaction, a mixture of stereoisomeric [3+2] cycloadductswasformed, in which one cycloadduct was obtained with a major quantity (10/1) (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Unveiling the Origin of the Selectivity and the Molecular Mechanism in the [3+2] Cycloaddition Reaction of N-aryl-C-carbamoylnitrone with N-arylitaconimide

Nacereddine

Chafaa

2022

Organics

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The [3+2] cycloaddition reaction of N-aryl-C-carbamoylnitrone (nitrone 1) with N-arylitaconimide (ethylene 2) was computationally studied using the B3LYP/6-31G(d) level of theory. An analysis of the different energetic profiles and the transition states’ optimized structures clearly indicated that this 32CA occurred through a non-polar, asynchronous, one-step mechanism, favoring the formation of the ortho–endo cycloadduct, as observed experimentally. The analysis of the reactivity indices derived from the conceptual DFT explains well the low polarity of this 32CA reaction. Parr functions and a dual reactivity descriptors analysis correctly explained the regioselectivity ortho of this 32CA reaction. Solvent effects did not modify the obtained selectivity but it increased the activation energies and decreased the exothermic character of this 32CA reaction. A thermodynamic parameters analysis indicated that this 32CA wascharacterized by an ortho regioselectivity and endostereoselectivity and exothermic and exergonic characters.

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A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides

Cited by 12 publications

References 65 publications

Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines

Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines

A Review on the Synthesis and Applications of α‐Alkylidene Succinimides

Unveiling the Origin of the Selectivity and the Molecular Mechanism in the [3+2] Cycloaddition Reaction of N-aryl-C-carbamoylnitrone with N-arylitaconimide

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