E–Z isomerization of 3-benzylidene-indolin-2-ones using a microfluidic photo-reactor

Abstract

(E)-3-Benzylidene-indolin-2-ones were efficiently converted to their corresponding (Z) -isomers at low temperature in the presence of light.

Structural Optimization, Anti‐TNBC Activities Evaluation, and Molecular Docking of an Indolone Derivative from Periplaneta americana

“…The specific structure of (E)-isomer and (Z)-isomer could be distinguished by their 1 H NMR characteristic. According to the literature, [35][36] the chemical shift of H placed in C=C of (E)-isomer was higher than that of (Z)-isomer (Figure 2B). Actually, the inconsistency mentioned about could be comprehended.…”

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

“…The E–Z isomerization of 3-benzylidene-2-ones was performed in a microfluidic photoreactor, both with an artificial light source and with solar irradiation (Scheme ). For optimization, the influence of solvent, residence time, light source and temperature were investigated on a milligram scale. DMF was chosen as solvent and best results (76% LC-MS yield, 71% isolated yield) were obtained when irradiating the reaction mixture for 15.7 min with a medium-pressure mercury lamp (250 W) at 10 °C.…”

Blue LED-Mediated Synthesis of 3-Arylidene Oxindoles

“…The internal olefin isomerization of representative products of 5 was successfully carried out in toluene under reflux conditions (Scheme ). On the other hand, the reaction of the E -isomer of 3-arylidene oxindoles 5o 1 in the presence of blue LED provided Z -isomer 5o 2 in only 14% yield.…”