Recyclable Magnetic MOF-Catalyzed Synthesis of 1-Aminoisoquinolines and 6-Aminophenanthridines from 5-(2-Bromoaryl)tetrazoles and 1,3-Diketones under Microwave Irradiation

Pham Duy Quang Dao, Seong Weon Lee, Ho Jin Lim, Chan Sik Cho

Research output: Contribution to journalArticlepeer-review

Abstract

In this study, 5-(2-bromoaryl)tetrazoles were reacted with 1,3-diketones in DMF in the presence of a catalytic amount of magnetic Cu-MOF-74 (Fe3O4@SiO2@Cu-MOF-74) and a base under microwave irradiation to yield the corresponding 1-aminoisoquinolines. The Fe3O4@SiO2@Cu-MOF-74 catalyst could be easily recovered from the reaction mixture and reused four times without any significant loss of catalytic activity. An initial copper-catalyzed C(sp2)-C(sp3) bond formation accompanied by retro-Claisen deacylative cyclocondensation (for acyclic 1,3-diketones) and direct cyclocondensation (for cyclohexane-1,3-diones) is proposed as a key reaction pathway for this process. Cyclohexanone-fused 1-aminoisoquinolines produced from the reaction between 5-(2-bromoaryl)tetrazoles and cyclohexane-1,3-diones could be aromatized into 6-aminophenanthridines via a one-pot sequential process involving reduction, dehydration, and oxidation.

Original languageEnglish
JournalJournal of Organic Chemistry
DOIs
StateAccepted/In press - 2024

Fingerprint

Dive into the research topics of 'Recyclable Magnetic MOF-Catalyzed Synthesis of 1-Aminoisoquinolines and 6-Aminophenanthridines from 5-(2-Bromoaryl)tetrazoles and 1,3-Diketones under Microwave Irradiation'. Together they form a unique fingerprint.

Cite this