[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

Abstract

Preliminary experiments shows, that [3+2] cycloadditions reactions proceeds with full regioselectivity and high stereoselectivity. In consequence, 3,4-trans-2-methyl-3-(3,4,5trimethoxyphenyl)-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.

[3+2] Cycloaddition Reaction of C‐Phenyl‐N‐methyl Nitrone to Acyclic‐Olefin‐Bearing Electron‐Donating Substituent: A Molecular Electron Density Theory Study

“…C ‐aryl‐ N ‐methyl nitrones serve as starting materials for synthesis of numerous novel isoxazolidine heterocycles in organic chemistry. C ‐aryl‐ N ‐alkyl nitrones have been employed to synthesize novel bioactive compounds . Recently, in 2017, 4‐nitroisoxazolidines have been regio‐ and steroselectively synthesized from 32CA reactions of C,N ‐diaryl nitrones.…”

Regiospecific formation of the nitromethyl-substituted 3-phenyl-4,5-dihydroisoxazole via [3 + 2] cycloaddition

“…The synthetic potential of the use of ∆ 2 -isoxazolines was explored in syntheses of β -hydroxyketones, γ -aminoalcohols, α , β -unsaturated oximes, and β -hydroxynitriles [ 6 ]. Applications of nitrosubstituted isoxazole derivatives in the field the chemistry and biochemistry are additionally also a logical consequence of (a) the wide range of theoretically possible channels of transformation of nitro group into other functional groups [ 7 , 8 ] and (b) the influence of the nitro group on the biological activity [ 9 , 10 ].…”

A DFT computational study on the [3+2] cycloaddition between parent thionitrone and nitroethene

“…It should be noted at this point that, in the case of [3+2] cycloadditions involving conjugated nitroalkenes, a one-step-mechanism may compete with a two-step, zwitterionic mechanism. This has been recently explored with regards to [3+2] cycloadditions of (Z)-C-anthryl-N-arylnitrones 23,29 and (Z)-C-(4-methoxyphenyl)-N-phenylnitrone with 1-chloro-1-nitroethene. 27 In consequence two different mechanisms should be considered for the considered reaction studied (Scheme 2).…”