An efficient, three‐component synthesis of spiro[benzo[g]chromene‐4,3′‐indoline]‐3‐carbonitrile and spiro[indoline‐3,5′‐pyrano[2,3‐d]pyrimidine]‐6′‐carbonitrile derivatives

Abstract

magnified image Spiro[benzo[g]chromene‐4,3′‐indoline]‐3‐carbonitriles and spiro[indoline‐3,5′‐pyrano[2,3‐d]pyrimidine]‐6′‐carbonitriles were synthesized via a three‐component reaction of isatins, 2‐hydroxynaphthalene‐1,4‐dione or 2‐methylpyrimidine‐4,6‐diol, and malononitrile in aqueous media. J. Heterocyclic Chem., (2009).

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 Novel Method for the Synthesis of Spiro[indoline‐Pyrazolo[4′,3′:5,6]pyrido[2,3‐d]pyrimidine]triones by Alum as a Reusable Catalyst

“…In continuation of our previous works for the synthesis of heterocyclic compounds [25–30], recently, we reported novel one‐pot, three‐component synthesis of spiro[indoline‐pyrazolo[4′,3′:5,6]pyrido[2,3‐d]pyrimidine]trione in refluxing condition at 24 h [31]. Herein, we report a simple and efficient method for the synthesis of these spirooxindoles with fused pyrazole, pyridine, and pyrimidine rings, through the three‐component one‐pot reaction in ionic liquid media, using Alum as a catalyst at very short reaction times.…”

Rapid and catalyst free synthesis of new bis(benzo[g]chromene) and bis(pyrano[3,2-c]chromene) derivatives and optimization of reaction conditions using response surface methodology

“…34 Therefore, the synthesis of these class of chromene compounds has fascinated much noticed in organic synthesis and many researchers have reported synthesis of these important compounds over the past few years. [35][36][37][38][39][40][41][42][43][44][45][46][47][48][49] Ketene dithioacetals are important precursors in organic synthesis of a variety of heterocyclic compounds and they have received increasing attention recently. [50][51][52][53][54] As part of our continuing research to be develop novel methods for multicomponent synthesis of new biologically active heterocyclic compounds from dithioacetals and because of the importance of using RSM in optimization of reaction conditions, herein, we report an efficient synthesis of 4,4 0 -(1,4-phenylene)bis(2-(alkylamino)-3-nitro-4H-benzo[g]chromene-5,10-dione) and 4,4 0 -(1,4-p henylene)bis(2-(alkylamino)-3-nitropyrano[3,2-c]chromen-5(4H)one) derivatives via one-pot, multi-component reaction of various amines, 1,1-bis(methylthio)-2-nitroethene (nitro ketene dithioacetal), terephthalaldehyde or isophthalaldehyde, and 2-hydroxy-1,4-naphthoquinone or 4-hydroxycoumarin in EtOH/H 2 O (85 : 15) at 89 C without any catalyst.…”