An Expedient Regio- and Diastereoselective Synthesis of Hybrid Frameworks with Embedded Spiro[9,10]dihydroanthracene [9,3′]-pyrrolidine and Spiro[oxindole-3,2′-pyrrolidine] Motifs via an Ionic Liquid-Mediated Multicomponent Reaction

• Published in: Molecules (Basel, Switzerland) Vol. 20; no. 9; pp. 16142 - 16153
• Main Authors: Arumugam, Natarajan, Almansour, Abdulrahman, Kumar, Raju, Menéndez, J., Sultan, Mujeeb, Karama, Usama, Ghabbour, Hazem, Fun, Hoong-Kun
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 01.09.2015; MDPI
• Subjects: 1,3-dipolar cycloaddition reactions; Anthracenes - chemical synthesis; Anthracenes - chemistry; Cancer; Cell cycle; Chemotherapy; Cycloaddition Reaction; Green chemistry; Humans; Indoles - chemical synthesis; Indoles - chemistry; ionic liquids; Models, Molecular; Molecular Structure; multicomponent reactions; Solvents; spirooxindoles; spiropyrrolidines; Saudi Arabia; Riyadh Saudi Arabia; multicomponent reactions; spirooxindoles; 1,3-dipolar cycloaddition reactions; ionic liquids; spiropyrrolidines
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules200916142

A series of hitherto unreported anthracene-embedded dispirooxindoles has been synthesized via a one-pot three-component 1,3-dipolar cycloaddition reaction of an azomethine ylide, generated in situ from the reaction of isatin and sarcosine to 10-benzylideneanthracen-9(10H)-one as a dipolarophile in 1-butyl-3-methylimidazolium bromide([bmim]Br), an ionic liquid. This reaction proceeded regio- and diastereoselectively, in good to excellent yields.