Three‐component 1,3‐dipolar cycloaddition reactions in synthesis of spiro[pyrrolidine‐2,3′‐oxindoline] derivatives

Abstract

Regio-and

Synthesis and regiochemistry of spiro indane-1,3-dione compounds

“…Several researchers have reported 1,3-dipolar cycloaddition reactions giving the regioisomers, and some have tried to explain the reasons by use of theoretical methods [7,8]. It is a common view that the azomethine ylide is initially generated in situ, via decarboxylative condensation of ninhydrin with proline, and is then trapped by the alkene to construct a new five-membered ring [9].…”

Crystal structure of 2-spiro-3′-(2-oxindole)-3-benzoyl-4-phenyl-5- hydroxymethylpyrrolidine, C25H22N2O3

“…The 1,3-dipolar cycloaddition reaction has also been employed for the construction of spiro-[pyrrolidine-2,3'-oxindoline] derivatives. Alkene derivatives, such as chalcone, acrylate, maleimide, maleic anhydride 2-arylidene-1-tetralone and arylidenemalononitrile derivatives, have been efficiently used as trapping dipolarophiles [4][5][6]. Almost all these reactions are in good yield and high regio-and stereo-selectivity.…”

Microwave-Assisted, Multicomponent, Ecofriendly Synthesis of 3-Bihetaryl-2-oxindole Derivatives Grafted with Phenothiazine Moiety

“…According to these prior observations and in continuation of our continous studies on synthesis of biologically active 2-oxindole derivatives, [19][20][21][22] we report herein the synthesis of several new pyrrole, phenothiazine, triazole, and 3-substituted 2-oxindole hybrids. The combination of these pharmacophores constrained in one scaffold is considered an efficient approach for the synthesis of more active, selective, and less toxic compounds of the expected wide range of biological activities.…”