Hamzehloueian, Mahshid published the artcileAn experimental and theoretical study on the regioselective synthesis of a new class of spiropyrrolothiazoles with quinoxaline motifs via a 1,3-dipolar cycloaddition reaction. An evaluation of DFT methods, Quality Control of 5153-73-1, the publication is RSC Advances (2015), 5(93), 76368-76376, database is CAplus.
A series of novel spiropyrrolothiazoles I (R = Ph, 4-MeC6H4, 2-O2NC6H4, 2-furyl, 2-thienyl, 1-naphthyl, etc.) with quinoxaline motifs was synthesized by a four-component 1,3-dipolar cycloaddition reaction of various trans-β-nitroalkenes RCH:CHNO2 and an azomethine ylide, generated in situ from 1,3-thiazolidine-4-carboxylic acid, ninhydrin and 1,2-phenylenediamine. The stereochem. of the products was confirmed by single crystal X-ray structure and spectroscopic techniques. Theor. calculations were carried out using DFT methods at the B3LYP/6-31G(d,p), wB97xD/6-31G(d,p) and M06-2X/6-31G(d,p) levels. The regio- and stereoselectivity was explained on the basis of transition state stabilities and global and local reactivity indexes of the reactants. The assessment of geometries and energetics of transition states revealed the importance of π/π interactions between aromatic rings in the regioselectivity of the cycloaddition reaction. The B3LYP functional was unable to deal with this weak interaction in the proposed TSs and led to an incorrect conclusion about the reaction regioselectivity. In this report, wB97xD and M06-2X functionals to calculate the transition states relative energies were successfully employed.
RSC Advances published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Quality Control of 5153-73-1.
Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts