The Three‐Component Reaction between Isatin, α‐Amino Acids, and Dipolarophiles

Abstract

Keywords: α-Amino acid / Cycloadditions / Nitrogen heterocycles 3-Spiro[pyrrolidino-oxindoles] were prepared in high yields from a three-component reaction between isatin, an α-amino acid, and a dipolarophile. Both N-substituted and N-unsubstituted α-amino acids were used as the amine component.

Molecular diversity of spirooxindoles. Synthesis and biological activity

“…Both N-unsubstituted and N-substituted α-amino acids have been employed in the study [80]. Thus, a series of spiro The method utilizing azomethine ylides, derived from isatin 114 and sarcosine 63 or L-proline 74, with ether linked α, β-unsaturated-β − C-glycosidic ketones 135 (R=β − Cglycosidyl) as a dipolarophiles was proposed by the same authors (Scheme 28) [83].…”

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

“…We noticed that the EWG, for example ester1 and benzoyl group [2,6], almost always connects with C-3 of the newly constructed pyrrolidine or pyrrolidine in the compounds previously synthesized by this method. 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].…”

“…Introduction 1,3-Dipolar cycloaddition is an efficient and general method for synthesis of fivemembered heterocyclic compounds, for example pyrrolidines, pyrrolines, and pyrroles [1][2][3]. During these three-species reactions, azomethine ylides are first generated in situ, and can be trapped smoothly by dipolarophiles, forming fivemembered heterocyclic compounds [4].…”

“…During these three-species reactions, azomethine ylides are first generated in situ, and can be trapped smoothly by dipolarophiles, forming fivemembered heterocyclic compounds [4]. Almost all these reactions proceed in good yield and with high regioselectivity and stereoselectivity [1][2][3][4]. Until now, however, scarcely any attention has been paid to the effect on selectivity of different alkenes.…”

Facile Three-Component Synthesis of Spirooxindolepyrrololine Ring Systems via 1,3-Dipolar Cycloaddition with 1,4-Naphthoquinone

“…[3][4][5][6] In 2001, Azizian et al [7] published a study of some reactions of proline (2a), isatin (1a), and N-arylmaleimide in refluxing ethanol, which are the conditions that yielded the pyrrolidine-2-spiro-3 0 -oxindole derivatives. Recently, Bergman et al [8] performed 1,3-dipolar cycloadditions involving different dipolarophiles such as N-benzylmaleimide and an azomethine ylide prepared from the decarboxylative condensation between N-substituted a-amino acids and isatin under reflux at 90 C in a mixture of methanol and water. This type reaction can also be performed under microwave conditions.…”