One‐pot synthesis of spiro[diindeno[1,2‐b:2′,1′‐e]pyridine‐11,3′‐indoline]‐triones

Abstract

A one-pot and pseudo four-component synthesis of spiro[diindeno[1,2-b:2 0 ,1 0 -e]pyridine-11,3 0 -indoline]-trione derivatives by cyclo-condensation reaction of isatins, 1,3-indandione, and ammonium acetate in refluxing acetic acid is reported.

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.…”

Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

“…2) as the main product, in which the arylamine only provided the amino group to form the pyridyl ring [16–21]. There are only very few papers describing that either 2-naphthylamine [22–25], functionalized 5-aminopyrazoles [26–28], or 2-aminobenzothiazoles [29] reacted with isatin and cyclic 1,3-dicarbonyl compounds to give the similar spiro[dihydropyridine-oxindole] ( II , III in Fig. 2), in which both the amino group and the aryl ring were involved in the construction of the pyridyl ring.…”

“…Although at present the exact mechanism of this three-component reaction is not very clear, a plausible reaction mechanism for the formation of spiro[dihydropyridine-oxindoles] is presented based on the similar multicomponent reactions of isatins [22–29]. Firstly, the reaction of isatin with one equivalent of cyclopentane-1,3-dione in acetic acid forms an aldol adduct ( A in Scheme 3).…”

One‐Pot Three‐Component Synthesis of Spirooxindoles Catalyzed by Hexamethylenetetramine in Water

“…Spirooxindoles occupy an important place in the area of heterocyclic chemistry because they are frequently found in numerous natural and synthetic products along with useful biopharmaceutical, physiopharmaceutical, and pharmaceutical activities . As a consequence, great efforts have been devoted to the construction of diversely structured spirooxindole‐fused heterocycles in the past few years . However, there have been few reports on the synthesis of one unique spirocyclic oxindole, incorporating a 2‐amino‐4 H ‐pyran‐3‐carbonitrile ring at the C3 position of oxindole .…”