Selective Synthesis of Functionalized Spiro[indoline-3,2′-pyridines] and Spiro[indoline-3,4′-pyridines] by Lewis Acid Catalyzed Reactions of Acetylenedicarboxylate, Arylamines, and Isatins

Abstract

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.

Chemoselective cyclization of 3-arylamino-2-hydroxy-tetrahydroindol-4-one in water at room temperature

“…1 [8]. During recent years, many researchers have described synthesis of indole and its derivatives along with its applications in the literature [9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20]. For example in 2017 Hao et al.…”

Molecular Design, Synthesis, Computational Screening, Antimicrobial Evaluation and Molecular Docking Study of Acetylinic Isatin Hybrids

“…It is an endogenous compound that acts as a versatile chemical building block for combinatorial library synthesis of compounds with potential drug profile . Easy synthesis, selective functionalization and intense pharmacological activity have collectively made this moiety the focus of active research area over the years . Isatin and its derivatives exhibit a multiplicity of biological activities ranging from antibacterial, antiviral, antifungal, anti‐inflammatory, antiangiogenic, antitumor, anticonvulsant, anti‐HIV, antitubercular, antiepileptic to sedative activity .…”

One-pot four-component reaction for convenient synthesis of functionalized 1-benzamidospiro[indoline-3,4'-pyridines]

“…In fact, the four-component reaction of hydrazine, acetylenedicarboxylate, isatin and malononitrile for the formation of spiro[indoline-3,4'-pyrano[2,3-c]pyrazoles] have been developed very recently by several groups [ 25 – 27 ]. Against this background and in continuation of our efforts toward the development of practical multicomponent reactions based on the reactivity of isatin and its derivatives [ 28 – 34 ], we herein wish to report the efficient synthesis of functionalized 1-benzamidospiro[indoline-3,4’-pyridines] via one-pot four-component reactions of benzohydrazide, acetylenedicarboxylate, isatin and malononitrile.…”