Transition‐Metal‐Free Reverse Reactivity of (2‐Alkynyl)‐Arylaldimines: Assembly of Functionalized Amino‐Indinones. Issue 5 (16th January 2020)

• Record Type: Journal Article
• Authors: Saini, Kapil Mohan; Saunthwal, Rakesh K.; Sushmita, ; Verma, Akhilesh K.
• Is Part Of: Chemistry. Volume 26:Issue 5(2020)
• Page Start: 1017
• Page End: 1021
• Publication Date: 2020-01-16
• Subjects: amino-indinones -- ortho-alkynyl aldehyde -- primary amines -- regioselectivity -- transition-metal-free reactions; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201904294
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Transition‐metal‐free regioselective synthesis of functionalized amino‐indenones by the reaction of ortho ‐alkynylaldehydes with a broad range of primary amines by intramolecular cyclization has been described. The designed reaction proceeds through KOH‐mediated Prins‐type cyclization and DMSO‐promoted oxidation of the cyclopent‐2‐en‐1‐one system. The proposed mechanism and role of solvent were well supported by control experiments. For the first time, we have disclosed the reverse reactivity of (2‐alkynyl)‐arylaldimines in a super basic system. Abstract : Regioselective transition‐metal‐free synthesis of functionalized amino‐indenones by the reaction of ortho ‐alkynylaldehydes with a broad range of primary amines by intramolecular cyclization has been described (see scheme). The designed reaction proceeds via KOH‐mediated Prins‐type cyclization and DMSO‐promoted oxidation of cyclopent‐2‐en‐1‐one system.