MEDT insights into the mechanism and selectivity of the (3 + 2) cycloaddition of (<i>Z</i>)-<i>N</i>-methyl-<i>C</i>-(2-furyl)-nitrone with but-2-ynedioic acid and the bioactivity of the reaction products.

ABSTRACT: In this contribution, Molecular Electron Density Theory (MEDT) is employed to investigate the (3 + 2) cycloaddition reaction between (Z)-N-methyl-C-(2-furyl)-nitrone 1 and but-2-ynedioic acid 2. DFT calculations at the M06-2X-D3/6-311+G(d,p) level of theory under solvent-free conditions at room temperature show that this reaction proceeds viaCA3-Z diastereoselectivity, with the formation of the CA3-Z cycloadduct being both thermodynamically and kinetically more favoured than the CA4-Z one. Reactivity parameters obtained from CDFT calculations reveal that compound 1 predominantly behaves as a nucleophile with moderate electrophilic features, in contrast to compound 2, which demonstrates strong electrophilicity and limited nucleophilic ability. This disparity in e

SUBMITTER: Chellegui M 

PROVIDER: S-EPMC12415692 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature