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1.

(3+2) Cycloaddition reactions with the participation of hetarene N-oxides: A review Pages 665-674 Right click to download the paper Download PDF

Authors: Roman Nahatskyi, Agnieszka Łapczuk

doi 10.5267/j.ccl.2026.3.004 Crossmark

Keywords: Isoxazolidine, Cycloaddition, Hetarene N-oxides, Stereoselectivity, Regioselective functionalization

Abstract:
This review presents the current state of knowledge on the (3+2) cycloaddition (32CA) reactions involving heteroarene N-oxides. While aromatic amine oxides behave similarly to nitrones, their participation in cycloaddition processes is chemically distinct due to the thermodynamic stability of the aromatic ring system. The manuscript critically examines these reactions, focusing on the competition between the formation of stable fused isoxazolidines and the tendency toward rearomatization. The latter often leads to spontaneous ring opening, elimination, or complex rearrangements rather than the isolation of the primary cycloadduct.
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Journal: CCL | Year: 2026 | Volume: 15 | Issue: 3 | Views: 30 | Reviews: 0

 
2.

1,2,4-Triazolyl thioacetamides: Design, synthesis, and photoelectrochemical properties Pages 231-242 Right click to download the paper Download PDF

Authors: Vamshikrishna Y. Radhakrishna, Gopal L. Khatik, Sakthivel Kandaiah, Vipin A. Nair

doi 10.5267/j.ccl.2026.2.005 Crossmark

Keywords: 1, 2, 4-Triazoles, N-Phenyl-2-thiocyanatoacetamide, 2-Chloro-N-phenylacetamide, Cycloaddition, Photoelectrochemical properties

Abstract:
Attempts to synthesize N-phenyl-2-((5-phenyl-4H-1,2,4-triazol-3-yl)thio)acetamide was unsuccessful via cycloaddition reaction between the N-phenyl-2-thiocyanatoacetamide and benzohydrazide in the presence of Lewis acid. During this procedure, a side product, 2-(phenylamino)thiazol-4(5H)-one is obtained through intramolecular cyclization. However, nucleophilic substitution reactions performed between 5-phenyl-4H-1,2,4-triazole-3-thiol and 2-chloro-N-arylacetamides in the presence of K2CO3 yielded a series of 4H-1,2,4-triazole-tethered acetamides in aqueous medium. The procedure affords excellent yields of desired products containing electron-withdrawing and electron-donating groups on the aromatic rings in a short reaction time with ease of operation. The oxidation potential and photocurrent measurements of the targets indicated that the presence of the electron-withdrawing substituents afforded better results with a lower oxidation potential and higher photocurrent measurements.
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Journal: CCL | Year: 2026 | Volume: 15 | Issue: 2 | Views: 181 | Reviews: 0

 
3.

On the question of the correlation between kinetic Dimroth parameters and global electron density transfer in [4+2]-π-electron cycloaddition reactions Pages 265-270 Right click to download the paper Download PDF

Authors: Karolina Kula, Agnieszka Łapczuk, Przemysław Woliński, Mikołaj Sadowski

doi 10.5267/j.ccl.2024.12.001 Crossmark

Keywords: Cycloaddition, Polarity, Solvent effect, Electron transfer

Abstract:
The correlation between coefficients from Dimroth equations and descriptors of global electron density transfer was explored based on the data available in the recent literature. We established that the obtained results should be very usable for the interpretation of the organic reactivity and molecular mechanisms.
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Journal: CCL | Year: 2025 | Volume: 14 | Issue: 2 | Views: 450 | Reviews: 0

 
4.

Recent progress in the field of cycloaddition reactions involving conjugated nitroalkenes Pages 13-38 Right click to download the paper Download PDF

Authors: Agnieszka Łapczuk-Krygier, Agnieszka Kącka-Zych, Karolina Kula

doi 10.5267/j.ccl.2018.12.002 Crossmark

Keywords: Cycloaddition, Conjugated Nitroalkenes, CNA

Abstract:
In this review we present recent progress in the cycloaddition reactions of conjugated nitroalkenes with alkenes, conjugated 1,3-dienes or three atoms components (eg. nitrones, azides, diazocompounds, azomethine imines and ylides).
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Journal: CCL | Year: 2019 | Volume: 8 | Issue: 1 | Views: 2242 | Reviews: 0

 
5.

[3+2] Cycloadditions of 1-halo-1-nitroethenes with (Z)-C-(3,4,5-trimethoxyphenyl)-N-methyl-nitrone as regio- and stereocontrolled source of novel bioactive compounds: preliminary studies Pages 123-128 Right click to download the paper Download PDF

Authors: Radomir Jasiński, Ewa Dresler, Maria Mikulska, Daniel Polewski

doi 10.5267/j.ccl.2016.2.001 Crossmark

Keywords: Cycloaddition, Nitroalkenes, Nitrones, Reactivity, Regioselectivity

Abstract:
Preliminary experiments shows, that [3+2] cycloadditions reactions proceeds with full regioselectivity and high stereoselectivity. In consequence, 3,4-trans-2-methyl-3-(3,4,5-trimethoxyphenyl)-4-halo-4-nitroisoxazolidines are forming as predominantly (or sole) products. Additionally, prognosis for the synthesized compounds to be potential ingredients of drugs is good.
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Journal: CCL | Year: 2016 | Volume: 5 | Issue: 3 | Views: 2550 | Reviews: 0

 
6.

An experimental and quantumchemical study of [2+3] cycloaddition between (Z)-C-(m,m,p-trimethoxyphenyl)-N-(p-methyphenyl)-nitrone and (E)-3,3,3-trichloro-1-nitroprop-1-ene: mechanistic aspects Pages 33-44 Right click to download the paper Download PDF

Authors: Alicja Szczepanek, Ewa Jasińska, Agnieszka Kącka, Radomir Jasiński

doi 10.5267/j.ccl.2014.10.003 Crossmark

Keywords: Nitrone, Cycloaddition, Kinetic, Mechanism, DFT calculations

Abstract:
Analysis of addent interactions with respect to the theory of electrophilicity and nucleophilicity indexes and kinetic studies shows the polar nature of [2+3] cycloaddition of (Z)-C-(m,m,p-trimethoxyphenyl)-N-(p-methylphenyl)-nitrone to (E)-3,3,3-trichloro-1-nitroprop-1-ene. However, PES exploration results do not confirm any zwitterion on the reaction paths. On the other hand, the nature of the solvent effect and the experimentally determined activation parameter values do not exclude a scenario in which one-step and stepwise processes occur simultaneously.
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Journal: CCL | Year: 2015 | Volume: 4 | Issue: 1 | Views: 2877 | Reviews: 0

 

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