I2/DMSO-Promoted the synthesis of chromeno[4,3‑b]quinolines through an imine formation/aza-Diels-Alder/aromatization tandem reaction under metal-catalyst and photosensitizer-free conditions

A tandem approach was developed for the efficient synthesis of substituted chromeno[4,3-b]quinolines from arylamines and O-cinnamyloxy salicylaldehydes under metal-catalyst and photosensitizer-free reaction conditions. Our protocol is based on an inexpensive I2/DMSO system in which molecular iodine first acts as a Lewis acid to promote the formation of the corresponding imine bearing the alkene moiety, then, this species fulfills a second role by catalyzing the intramolecular aza-Diels-Alder cycloaddition to generate the respective tetrahydro-chromenoquinolines as an intermediates. Finally, the dual behaviour of DMSO as an oxidant and as a solvent resulted crucial at this stage, allowing the regeneration of I2 and promoting the aromatization of the tetrahydro-chromenoquinoline intermediates to yield the desired 7-aryl-6H-chromeno[4,3-b]quinolines. This protocol features by being mild, easy to perform, high step-economy (tandem process) and for providing a new access to biologically important nitrogen and oxygen containing heterocyclic molecules.

Tandem Olefin Metathesis/α-Ketohydroxylation Revisited

EWG-activated and polar quaternary ammonium salt-tagged ruthenium metathesis catalysts have been applied in a two-step one-pot metathesis-oxidation process leading to functionalized α-hydroxyketones (acyloins). In this assisted tandem process, the metathesis catalyst is used first to promote ring-closing metathesis (RCM) and cross-metathesis (CM) steps, then upon the action of Oxone™ converts into an oxidation catalyst able to transform the newly formed olefinic product into acyloin under mild conditions.

Degradation pathway of triazole fungicides and synchronous removal of transformation products via photo-electrocatalytic oxidation tandem MoS2 adsorption

A simple and effective tandem process of photo-electrocatalytic oxidation (PECO)-MoS2 adsorption was developed for the synchronous removal of triazole fungicides (TFs) and toxicological transformation products (TPs). In order to accurately identify trace TPs and evaluate degradation pathway during water treatment, a sensitive analytical method was developed on the basis of the stir bar sorptive extraction (SBSE) pretreatment tandem LC-MS/MS technique. Firstly, the typical TFs (PRO, TET, and DIN, C0 = 1.0 mg/L) in actual water samples were treated under the optimal process (bias voltage 1.8 V, pH 4, irradiation intensity 50 mW/cm2, 0.05 g MoS2/100 mL, 350 rpm, adsorption of 5 min). The result indicated that the residues of PRO, TET, and DIN in secondary effluent were 0.0973, 0.0617, and 0.0012 mg/L, respectively, with the removal rates of 90.3%, 93.8%, and 99.9%, respectively, undergoing 30-min photo-electrocatalysis and 5-min adsorption. The alkaline medium was favorable for the adsorption of MoS2 to TFs. The assessment results of potential cancer risk indicated that the residues of TFs in secondary effluent were safe for drinking water consumption. Besides, the major TPs were identified via the SBSE-HRLC-MS/MS technique, and one possible transformation pathway of TFs was proposed. TFs mainly underwent dehydrochlorination, cyclization, hydroxylation, etc. to produce a series of nitrogenous heterocyclic compounds that possess higher polarity than parents, hinting that TPs might pose potential aquatic toxicity. However, TPs can be removed synchronously by this tandem technique. The current study can provide a theoretical basis for the harmless treatment of TFs in the water environment.

Synthesis of 2-Chromanone-fused [3.2.0] Bicycles through a Phosphine-mediated Tandem [3+2] Cyclization/Intramolecular Wittig Reaction

A phosphine-mediated tandem [3+2] cyclization/intramolecular Wittig reaction of 3-aroylcoumarin with alkynone is described. The high efficiency of tandem process allows the synthesis of 2-chromanone-fused bicyclo[3.2.0]heptenones in moderate to high yields...

Copper-catalyzed tandem annulation of 2-alkynoyl-2′-iodo-1,1′-biphenyls with isocyanoacetates: a rapid access to pyrrole-fused tetracyclic skeletons

A copper-catalyzed [3 + 2] cycloaddition/C–C coupling tandem process was developed based on the concept of trapping organocuprate intermediates.

CO2 hydrogenation to methanol and hydrocarbons over bifunctional Zn-doped ZrO2/zeolite catalysts

The tandem process of carbon dioxide hydrogenation to methanol and its conversion to hydrocarbons over mixed metal/metal oxide-zeotype catalysts is a promising path to CO2 valorization.