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Transition‐Metal‐Free Reverse Reactivity of (2‐Alkynyl)‐Arylaldimines: Assembly of Functionalized Amino‐Indinones
Author(s) -
Saini Kapil Mohan,
Saunthwal Rakesh K.,
Verma Akhilesh K.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904294
Subject(s) - regioselectivity , reactivity (psychology) , chemistry , intramolecular force , transition metal , combinatorial chemistry , solvent , metal , primary (astronomy) , stereochemistry , medicinal chemistry , catalysis , organic chemistry , medicine , physics , alternative medicine , pathology , astronomy
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.