One‐pot, three‐component synthesis of spironaphthopyrano[2,3‐d]pyrimidine‐5,3′‐indolines in water

Abstract

0 -indoline derivatives by cyclo-condensation reaction of isatins, 2-naphthol, and barbituric acids in aqueous media is reported.

Molecular diversity of spirooxindoles. Synthesis and biological activity

“…Thus, the procedures used water as a solvent in the presence of p-TSA as a catalyst [152]. Recently, two groups of authors identified dodecyl benzenesulfonic acid (DDBSA) functionalized by silica-coated magnetic nanoparticles (γ − Fe 2 O 3 @SiO 2 -DDBSA) [153] and KAl(SO 4 ) 2 · 12H 2 O in [Bmim]PF 6 [154] as an efficient catalysts for the synthesis of a library It was shown that refluxing of a mixture of barbituric acid 264, β-naphthol 266, and isatin 114 in water in the presence of catalytic p-TSA afforded the spironaphthopyranopyrimidineindolines 267 in good yields (Scheme 75) [155]. …”

Recent Progress on Routes to Spirooxindole Systems Derived from Isatin

“…With different Michael donors, diversely fused heterocycles with pyran or 1,4‐dihydropyridine moiety will be established. For example, the listed donors such as 3‐methyl‐1 H ‐pyrazol‐5(4 H )‐one , 4‐hydroxycoumarin , 4‐hydroxyquinolin‐2(1H)‐one and its N ‐allylic derivatives , cyclic 1,1‐enediamine , dimedone , 1‐(2‐phenylhydrazono)propan‐2‐one , β‐diketone or β‐ketoester , 2‐hydroxynaphthalene‐1,4‐dione , 3‐aminophenol , 2‐methyl pyrimidine‐4,6‐diol , 3‐methyl‐1 H ‐pyrazol‐5‐amine , naphthalen‐2‐amine , 1 H ‐indene‐1,3(2 H )‐dione , naphthalen‐2‐ol , and furan‐2,4(3 H ,5 H )‐dione are proved to be efficient for such protocol. Certainly, the suitable electron‐rich donors for such domino reaction are not limited to the aforementioned ones, and they can be reasonably extended to others with their functional group diversity.…”

A New Reaction of Isatin, Cyclic 1,3‐Diketone, and 2‐Cyanoacetamide: A Four‐Component Synthesis of Spirooxindoles

“…In continuation of our previous works on synthesis of spirooxindoles , herein, we envisioned that the use of 2‐cyanoacetamide instead of malononitrile or cyanoacetic esters in the three‐component reaction with isatins and 1,3‐dicarbonyl compounds might be a novel method to achieve new spirooxindole carboxamides 4 (Scheme ).…”