Ultrasound-assisted 1,3-dipolar cycloaddition and cyclopropanation reactions for the synthesis of bis-indolizine and bis-cyclopropane derivatives

Abstract

Ultrasound irradiation can promote the 1,3-dipolar cycloaddition reaction of 2-chloropyridinium ylides with 2-benzylidenemalononitrile or 2,2'-(1,4-phenylenebis(methanylylidene))dimalononitrile, to afford the indolizine and bis-indolizine derivatives respectively. While the reaction of pyridinium ylides with 2-benzylidenemalononitrile or 2,2'-(1,4-phenylenebis(methanylylidene))dimalononitrile under ultrasound irradiation provided, in an unusual manner, cyclopropane and bis-cyclopropane derivatives, respectively. These cycloaddition and cyclopropanation reactions were carried out in the presence of triethylamine, in acetonitrile, at room temperature.

KF/Al2O3 as a Recyclable Basic Catalyst for 1,3-Dipolar Cycloaddition Reaction: Synthesis of Indolizine-1-Carbonitrile Derivatives

“…24 But for the synthesis of further derivatives of these compounds and fix problems, we developed this method and used reaction of 1-alkyl-2-chloropyridinium According to the results obtained up to this point, we decided to apply this method for synthesis of mono indolizine-1-carbonitrile derivatives (4a-d) by using 1,3-dipolar cycloaddition reaction of 1-alkyl-2-chloropyridinium bromides (1a-d), malononitrile (2) and benzaldehyde (3) at reflux, in the presence of KF/Al 2 O 3 in ethanol ( Table 2). To explain the mechanism of this one-pot two-step tandem reaction, we propose a plausible reaction mechanism which is illustrated in Scheme 3.…”

Three-Component Synthesis of Mono and Bis 4,5-Dihydropyrano[3,2-C]Chromenes and 4,5- Dihydropyran[4,3-B]Pyrans Catalyzed by Sodium Benzenesulfinates as a Green Organocatalyst

“…9 It is not surprising that the synthesis of these compounds has received considerable attention, because PFHC play important roles in the synthesis of a large number of biologically active molecules. 10,11 In the recent years, a great deal of research into PFHC has permitted the synthesis of bisheterocyclic compounds that show various biological activities, such as antibacterial, fungicidal, tuberculostatic, and antiamoebic properties. [12][13][14] Among these aforementioned compounds, 4,5-dihydropyrano [3,2-c]chromene and 4,5-dihydropyrano [4,3-b]pyran derivatives have received much attention, due to their remarkable molecular structures and important biological 15 and pharmacological 16 applications.…”

Two ligand oxidio-vanadium(IV) complexes as novel efficient catalysts in multicomponent reactions for synthesis of tetrahydrobenzopyran derivatives

“…Moreover, in continuation of our studies on the synthesis of heterocyclic compounds by three-component reaction [29][30][31][32], the catalytic activity of these complexes was also investigated for multi-component reaction of dimedone (1a) or 1,3-cyclohexanedione (1b), malononitrile (2) and aromatic aldehydes (3a-r) in ethanol at reflux (Scheme 1) to remove the above mentioned drawbacks. Scheme 1.…”