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.
| Original language | English |
|---|---|
| Pages (from-to) | 1017-1021 |
| Number of pages | 5 |
| Journal | Chemistry - A European Journal |
| Volume | 26 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - 16 Jan 2020 |
Keywords
- amino-indinones
- ortho-alkynyl aldehyde
- primary amines
- regioselectivity
- transition-metal-free reactions
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