ABSTRACT
A novel Sn(ii)-catalyzed tandem cyclization reaction of aromatic aldehydes with ethyl cyanoacetate has been achieved to afford a series of 3-substituted azetidine-2,4-diones in good to excellent yields. This protocol provides straightforward access to construct the azetidine core through sequential Knoevenagel condensation, hydration and the C-N cyclization reaction.
ABSTRACT
An unexpected CsF-assisted C-N bond cleavage was exploited to synthesize highly functionalized and biologically important 1,4,5,6-tetrahydropyridazine derivatives from α-halo N-acylhydrazones in excellent yields. The extrusion of nitrogen and the [4 + 2] cycloaddition between in situ-generated azoalkenes is a key reaction in the process. The identified methodology is suitable for synthesizing a wide variety of analogues of tetrahydropyridazines, which are prevalent in many medicinally important small molecules. The reaction conditions are mild, high-yielding, and amenable for the gram scale.
ABSTRACT
A one pot, highly regioselective synthesis of racemic 3,3'-spiro-phosphonylpyrazole-oxindole by 1,3-dipolar cycloaddition of an in situ generated anion of dialkyl 1-diazomethylphosphonate from the Bestmann-Ohira reagent (BOR) & methyleneindolinones has been developed. The synthesis affords the highly functionalized pyrazole scaffolds in good yields with excellent regioselectivity under mild reaction conditions within a short reaction time.