A cascade reaction of 3-hydroxy-2-phenylisoindolin-1-one and cyclopropyl ketone has been developed
via
a BrØnsted acid-promoted ring-opening/intramolecular cross-cycloaddition/4 + 2-cycloaddition ...process. The developed methodology provides straightforward access to pentacyclic isoindolin-1-one derivatives under simple reaction conditions.
A cascade reaction of 3-hydroxy-2-phenylisoindolin-1-one and cyclopropyl ketone has been developed
via
BrØnsted acid-promoted ring-opening/intramolecular cross-cycloaddition/4 + 2-cycloaddition process.
We present the first example of visible-light-mediated multicomponent annulation of 1,7-diynes by taking advantage of quadruple cleavage olf carbon-halogen bonds of BrCCl
to generate a C1 synthon, ...which was adeptly applied to the preparation of skeletally diverse 3-benzoyl-quinolin-2(1
)-one acetates in moderate to good yields. Controlled experiments demonstrated that H
O acted as both oxygen and hydrogen sources, and
-dichlorovinyl carbonyl compound exhibited as a critical intermediate in this process. The mechanistic pathway involves Kharasch-type addition/6-exo-dig cyclization/1,5-(SN")-substitution/elimination/binucleophilic 1,6-addition/proton transfer/tautomerization sequence.
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A new method for the synthesis of heterocyclic systems containing tetrazole and tetrahydroisoquinoline is developed via the performance of one-pot Ugi-azide and Heck cyclization reactions. The ...integration of the multicomponent and post-condensation reactions in one-pot maximizes the pot-, atom-, and step-economy (PASE).
A new continuous flow synthetic method for preparing indole and its derivatives are successfully developed to overcome the disadvantages of traditional batch methods, such as low conversion rates, ...long reaction times, and amplification effects. The method represents a sustainable and efficient preparation of indole and its derivatives without the need for additional catalysts. By investigating the effects of the reaction temperature, the solvent, the equivalence ratio, and the residence time, high conversion rates and excellent yields were simultaneously achieved within 20 min under optimized conditions. For the template reaction, DMSO/H2O/AcOH = 2:1:1 is used as the solvent, the reaction temperature is 110 °C, and the ratio of phenylhydrazine hydrochloride to cyclopentanone is 1:1.05. Indole and a wide array of its derivatives are synthesized to verify the universality of the method, and most of the reactions exhibit satisfactory conversion rates and high yields are obtained. This new continuous flow method is more suitable for industrial scale-up relative to traditional batch methods.
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Two kinds of 3 + 2 cycloaddition intermediates generated from the three-component reactions of 2-bromobenzaldehydes and maleimides with amino esters or amino acids were used for a one-pot
-allylation ...and intramolecular Heck reactions to form pyrrolidinedione-fused hexahydropyrrolo2,1-
isoquinolines. The multicomponent reaction was combined with one-pot reactions to make a synthetic method with good pot, atom and step economy. MeCN was used as a preferable green solvent for the reactions.
The design and synthesis of a type of 1 + 4 + 2 four-layer framework have been conducted by taking advantage of Suzuki–Miyaura cross-coupling and group-assisted purification (GAP) chemistry. The ...optimized coupling of double-layer diboronic esters with 1-bromo-naphth-2-yl phosphine oxides resulted in a series of multilayer folding targets, showing a broad scope of substrates and moderate to excellent yields. The final products were purified using group-assisted purification chemistry/technology, achieved simply by washing crude products with 95% EtOH without the use of chromatography and recrystallization. The structures were fully characterized and assigned by performing X-ray crystallographic analysis. UV–vis absorption, photoluminescence (PL), and aggregation-induced emission (AIE) were studied for the resulting multilayer folding products.
Hydrolysis of 2-Chlorobenzal chloride is the primary production method of 2-chlobrobenzaldehyde in industry, but the reactor technologies and reaction processes of this method are traditional and ...underdeveloped, in which the dichotomous leaf hydrolysis agitator is commonly used, resulting in low efficiency during the hydrolysis process. In this article, ANSYS software was utilized to enhance the hydrolytic reactors used in industrial production by simulating and analyzing the dispersion characteristics of droplets in the reactor. The particle size distribution of dispersed phase droplets and the Sauter mean diameter (D32) were used to characterize the dispersion effect, and the dispersion characteristics of the dichotomous leaf agitator and the three-bladed back-curved impeller, three-bladed propeller impeller, open turbine impeller, and crescent impeller were compared and studied. The results showed that there was a log-linear relationship between the D32 of the dispersed phase and the stirring speed in different systems; the number of tiny droplets in the three-bladed back-curved impeller system increased remarkably, and the droplets size distribution width decreased significantly, achieving mass transfer enhancement in the hydrolysis reaction system. The reliability of the simulation results was verified by the measurement experiment using the Sauter mean diameter (D32) of dispersed phase droplets. The results showed that the Sauter mean diameter (D32) variation trend is consistent with that of the simulation, and the error between them is less than 10%. A lab-scale hydrolytic reactor was designed and produced based on the scheme of an industrial hydrolytic reactor equipped with a three-bladed back-curved impeller, the effect of the hydrolytic reaction was verified, and the process conditions were strengthened under the same conditions. The results showed that, compared with the case in the reactor using a dichotomous leaf hydrolysis agitator at the same reaction temperature and catalyst conditions, the reaction time of hydrolysis completion reduced to 58.33% at the lab-scale, and to 63.89% at the industrial-scale at the stirring rate of 446 r/min, using a three-bladed back-curved impeller. These results provide a technical scheme and a basis for process strengthening for improving the production efficiency of 2-chlorobenzaldehyde production equipment in industry.
Comprehensive Summary
A general and convenient photoredox‐catalyzed acylation and alkylcyanation of MBH acetates has been established, enabling the assembly of the C(sp2)–C(sp3) bond by a ...nitrogen‐centered radical strategy for the synthesis of trisubstituted alkenes in moderate to excellent chemical yields (48 examples in total). The reaction of MBH acetates with acyl (indanone) oxime esters afforded trisubstituted alkenes containing 1,4‐dicarbonyl groups. Interestingly, the use of Eosin Y as a photocatalyst in the catalytic system resulted in the formation of distal cyano group‐anchored trisubstituted alkenes via deconstructive functionalization of cycloketone oxime esters. Notably, these resulting 1,4‐dicarbonyl compounds could be applied to late‐stage transformations, providing important methods for the synthesis of dihydropyridazin‐3(2H)‐one.
A general and convenient photoredox‐catalyzed acylation and alkylcyanation of MBH acetates has been established, enabling the assembly of the C(sp2)–C(sp3) bond by a nitrogen‐centered radical strategy for the synthesis of trisubstituted alkenes in moderate to excellent chemical yields (48 examples in total).
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BFBNIB, FZAB, GIS, IJS, KILJ, NLZOH, NUK, OILJ, SAZU, SBCE, SBMB, UL, UM, UPUK
The first photocatalytic trichloromethyl radical-triggered annulative reactions of amide-linked 1,7-diynes with polyhalomethanes were established for the flexible assembly of functionalized ...quinolin-2(1H)-ones with generally acceptable yields. With the installation of the aryl group (R
) into the alkynyl moiety,
-center radical-initiated Kharasch-type addition/nucleophilic substitution/elimination cascade to produce quinolin-2(1H)-ones-incorporating
-dihaloalkene, whereas three examples of polyhalogenated quinolin-2(1H)-ones were afforded when amide-linked 1,7-diynes bearing two terminal alkyne units were subjected to BrCX
by exploiting dry acetonitrile as a solvent.
A new Pd(II)-catalyzed annulation/iododifluoromethylation of enynones has been developed for the synthesis of versatile 1-indanones with moderate to good yields (26 examples). The present strategy ...enabled the concomitant incorporation of two important difluoroalkyl and iodo functionalities into 1-indenone skeletons with (E)-stereoselectivity. The mechanistic pathway was proposed, consisting of the difluoroalkyl radical-triggered α,β-conjugated addition/5-exo-dig cyclization/metal radical cross-coupling/reductive elimination cascade.
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