An efficient synthetic procedure for the synthesis of functionalized tetrahydrospiro[indoline‐3,2′‐quinoline] derivatives was successfully developed and involves the four‐component reaction of arylamines, dimethyl acetylenedicarboxylate, isatins, and a cyclohexane‐1,3‐dione in acetic acid. The advantages of this reaction include the use of common starting materials and mild reaction conditions and it is operationally simple.
Spiro[indoline-3,3′-pyrrolizines] and spiro[indoline-3,7′-pyrrolo[1,2-a]azepines] can be selectively produced from three-component reaction of α-amino acids, isatins and but-2-ynedioates.
A practical procedure for the preparation of fused 1,4-dihydropyridines was developed through the domino four-component reactions of arylamines, acetylenedicarboxylate, aro-
SummaryIn the presence of p-toluenesulfonic acid as catalyst the domino reaction of arylamines, methyl propiolates and aromatic aldehydes in ethanol proceeded smoothly to give polysubstituted 1,2,3,4-tetrahydroquinolines in moderate yields. The reaction is believed to involve the Povarov reaction of in situ generated β-enamino ester with the in situ formed aromatic imine.
The functionalized spiro[indoline-3,2'-pyridine]-3',4',5',6'-tetracarboxylates were efficiently synthesized by BF3·OEt2-catalyzed reactions of isatin-3-imines with acetylenedicarboxylates in methylene dichloride. Under similar conditions, the BF3·OEt2-catalyzed three-component reactions of acetylenedicarboxylates, arylamines, and isatins afforded functionalized spiro[indoline-3,4'-pyridine]-2',3',5',6'-tetracarboxylates in moderate yields.
Domino reactions have attracted much high attention in recent years due to its convergence, productivity, facile execution and generation of highly diverse and complex products from easily available starting materials in a single operation. Addition of primary amines to electron-deficient alkynes could generated reactive enaminone (ester) in mild conditions, which have shown versatile reactivity and have been widely used in domino procedure as key reactive intermediate to develop a number of carbon-carbon bond formation reactions, heterocyclic and spiro cyclic constructions. In this paper the recent developments of the domino reactions with enamino esters as key intermediates based on our experimental investigation are reviewed.
SummaryThe four-component reaction of 2-aminobenzothiazole, aromatic aldehydes, acetylenedicarboxylate and piperidine or pyrrolidine in ethanol afforded the functionalized 2-pyrrolidinones containing both benzothiazolyl and piperidinyl (or pyrrolidinyl) units in good yields. On the other hand, the similar four-component reactions resulted in the functionalized morpholinium or piperidinium 2-pyrrolidinon-3-olates in the presence of p-toluenesulfonic acid.
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