Organic chemistry
Zahed Karimi-Jaberi; Abdolhossein Fereydoonnezhad
Volume 5, Issue 4, pp. 364-493, Serial No. 17 , October 2017, , Pages 407-416
Abstract
Spirooxindoles are important synthetic targets possessing extended biological activity and drug discovery applications.The development of multicomponent reactions designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal ...
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Spirooxindoles are important synthetic targets possessing extended biological activity and drug discovery applications.The development of multicomponent reactions designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal chemistry. in this Manuscript, a facile and efficient multicomponent synthesis of functionalized spirooxindoles has been described through the reaction of isatin, malononitrile or ethyl cyanoacetate, and CH- acids (1,3-dicarbonyl compounds) in the presence of catalytic amount of citric acid in excellent yields with short reaction times in aqueous ethanol. Also citric acid catalyzed synthesis of 3,3-diindolyl oxindoles by the condensation of isatin with substituted indoles.
Organic chemistry
Seyyedeh Cobra Azimi; Kurosh Rad-Moghadam
Volume 5, Issue 2, pp. 121-236, Serial No. 15 , April 2017, , Pages 156-166
Abstract
A practical and new method for the synthesis oxindole substituted pyrrolo[2,3-d]pyrimidines by the condensation of isatin, acetophenone and 6-amino-uracil under ultrasound irradiation conditions at 60 °C was described. The reaction was developed via a sequential tandem process to afford the oxindole ...
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A practical and new method for the synthesis oxindole substituted pyrrolo[2,3-d]pyrimidines by the condensation of isatin, acetophenone and 6-amino-uracil under ultrasound irradiation conditions at 60 °C was described. The reaction was developed via a sequential tandem process to afford the oxindole substituted pyrrolo[2,3-d]pyrimidines in good to excellent yields. All reactions performed efficiently under ultrasound irradiation and results were compared with conventional heating method. In this field, several types of acetophenones, amino-uracils, and isatins were rapidly changed to the corresponding derivatives. The remarkable features of the new procedure are shorter reaction time, excellent yields, cleaner reaction profile, and simple experimental and workup procedure.
Organic chemistry
Mohammad Javad Taghizadeh; Khosrow Jadidi
Volume 3, Issue 1, pp. 1-71, Serial No.6 , January 2015, , Pages 57-61
Abstract
An efficient one-pot three-component procedure for the synthesis of new chiral spiro oxindolopyrrolidines/pyrrolizidines with highly regio- and diastereo-enantio, selective from 1,3-dipolar cycloaddition of azomethine ylides and chiral menthol-drived trans-cinnamic are described. The mechanism of the ...
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An efficient one-pot three-component procedure for the synthesis of new chiral spiro oxindolopyrrolidines/pyrrolizidines with highly regio- and diastereo-enantio, selective from 1,3-dipolar cycloaddition of azomethine ylides and chiral menthol-drived trans-cinnamic are described. The mechanism of the reaction is discussed on basis of the assignment of the absolute configuration of one of the cycloaddition products, which obtained by single crystal X-ray analysis. The process occurs at reflux temperature in ethanol as green solvent and in the absence of any bidentate chelating Lewis acids. Functionalized pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds.1 Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems.