The First Examples of [3+2] Cycloadditions with the Participation of (E)-3,3,3-Tribromo-1-Nitroprop-1-Ene

Abstract

The first examples of [3+2] cycloaddition reactions between 3,3,3-tribromo-1-nitroprop-1-ene (TBMN) were explored on the basis of experimental and theoretical approaches. It was found that reactions involving TBMN and diarylnitrones realized with full regio- and stereoselectivity lead to respective 3,4-cis-4,5-trans-4-nitroisoxazolidines. The regioselecticity and the molecular mechanism of title processes was analyzed on the basis of the advanced DFT computational study.

Full Regio- and Stereoselective Protocol for the Synthesis of New Nicotinoids via Cycloaddition Processes with the Participation of Trans-Substituted Nitroethenes: Comprehensive Experimental and MEDT Study

“…This favors the formation of 3,4-cis configuration in the final adduct. An identical effect was recently detected in the case of many examples of the 32CAs between aryl-substituted TACs and conjugated nitroalkenes [29][30][31][32].…”

Nitrosubstituted analogs of isoxazolines and isoxazolidines: a surprising estimation of their biological activity via molecular docking.

“…We carried out molecular docking to estimate and compare the strength of non-covalent bonding between series of compounds under consideration and a series of various proteins already known to exhibit various kinds of activity with similar molecules as described further in a more detailed fashion. This work is sort of a continuation of our recent research of trihalomethylated isoxazole analogs, which were described in our previous papers [10][11].…”

“…There are many organic compounds with isoxazoline, isoxazolidine motif, that are known to exhibit biological activity in various fields such as antifungal, antibacterial, anti-inflammatory, antidepressant or anticancer ones [5][6][7][8][9]. In addition, presence of a trihalomethyl functional group in the heterocyclic ring, increases biocompatibility of the compound [10][11][12]. The most popular drug containing both isoxazoline ring and trihalomethylated group is Fluranarel (Figure 1), which is a strong antiparasite agent, widely used in veterinary with a broad spectrum of application [13].…”

(1E,3E)-1,4-Dinitro-1,3-butadiene—Synthesis, Spectral Characteristics and Computational Study Based on MEDT, ADME and PASS Simulation

“…For reaction progress testing, thin layer chromatography (TLC) was performed using aluminum plates with silica (unmodified layers) as the standard procedure in the case of nitrogen-containing organic compounds [ 74 , 75 , 76 ]. As the role of an eluent, cyclohexane–ethyl acetate mixture CyH:EtOAc (80:20 v / v ) was applied.…”