N-Heterocyclic carbene catalyzed intramolecular crossed aldehyde-ketone benzoin condensation in the chalcone of o-phthalaldehyde: a facile synthesis of naphthalenones |
| |
| Authors: | Shravankumar KankalaRavikrishna Edulla Sarangapani ModemRavinder Vadde Chandra Sekhar Vasam |
| |
| Institution: | a Department of Chemistry, Kakatiya University, Warangal 506 009, India
b Department of Chemistry, Satavahana University, Karimnagar 505 001, India |
| |
| Abstract: | The intramolecular crossed aldehyde-ketone benzoin condensation in the chalcone of o-phthalaldehyde (OPA) catalyzed by N-heterocyclic carbene (NHCs) generated in situ from readily available imidazolium and thiazolium salts is described. In this reaction, bicyclic α-hydroxyl ketones (naphthalenone type tertiary alcohol) were selectively produced in good yields (75-94%) in shorter reaction times (20 min) through nucleophilic addition of acyl anion generated by umpolung in OPA-chalcone (regio controlled). |
| |
| Keywords: | N-Heterocyclic carbene Intramolecular benzoin condensation Umpolung o-Phthalaldehyde Naphthalenone |
| 本文献已被 ScienceDirect 等数据库收录！ |
