Three-component assembly of stabilized fluorescent isoindoles

Abstract

The tandem addition of an amine and a thiol to an aromatic dialdehyde engages a selective three-component assembly of a stabilized fluorescent isoindole.

Application of Virtual Reality Technology in Teaching and Training System of Processing Industrial Robot

“…Maslivetc, V. A., builds a visual system to observe teaching tools. Once the system is calibrated, neither the robot nor the visual system can move, which limits the teaching space and movement range of the robot to a certain extent [6].…”

Synthesis and Atropisomeric Properties of Benzoazepine-Fused Isoindoles

“…The exception to this bench stability is the mesyl derivative 5d , which was observed to slowly decompose in solvents at room temperature (see the Supporting Information for details). This instability is possibly due to a lack of stabling π-stacking interactions with the sulfonamide, rendering the reactive isoindole fragment susceptible to typical decomposition pathways such as polymerization and auto-oxidation. , This remarkable isoindole stability is attributed to the −M effect of the electron-withdrawing nitro group, reducing the electron density of the isoindole and thus susceptibility to auto-oxidation decomposition pathways. ,,,, Additionally, substitution of the nitrogen, intramolecular π-interactions, and incorporation of the isoindole into a larger ring system may contribute further stabilizing effects. ,,,, …”

“…55,56 This remarkable isoindole stability is attributed to the −M effect of the electron-withdrawing nitro group, reducing the electron density of the isoindole and thus susceptibility to auto-oxidation decomposition pathways. 10,14,55,57,58 Additionally, substitution of the nitrogen, intramolecular π-interactions, and incorporation of the isoindole into a larger ring system may contribute further stabilizing effects. 6,8,56,59,60 As noted in the Introduction, the 1 H NMR resonances attributed to the methylene protons of the isoindoles (5) are AX doublets, indicating that the protons are diastereotopic (Figure 2).…”

“…This instability is attributed to the skewed electron density of the 10π ortho quinoid aromatic system toward the five-membered ring, consistent with the Glidewell–Lloyd rule, subsequently lowering the aromaticity of the six-membered ring . Nevertheless, with applications as fluorescent − and antiproliferative − materials (Figure a) and use as participants in numerous interesting cycloadditions (Figure b), − 2 H -isoindoles remain a valuable target for new synthetic methods.…”