A new rapid multicomponent domino reaction for the formation of functionalized benzo[h]pyrazolo[3,4-b]quinolines

Bo Jiang, Ge Zhang, Ning Ma, Feng Shi, Shu Jiang Tu, Parminder Kaur, Guigen Li

Research output: Contribution to journalArticlepeer-review

55 Scopus citations

Abstract

A new multicomponent domino reaction for rapid and regioselective synthesis of highly functionalized benzo[h]pyrazolo[3,4-b]quinolines has been established. The reaction can be conducted by using readily available and inexpensive substrates under microwave irradiation within short periods of 10-26 min. Good to excellent chemical yields (61-91%) and complete regioselectivity have been achieved for 22 examples. Tedious work-up procedure can be avoided due to the direct precipitation of products from the reaction solution. The resulting benzoquinolines have been readily converted into quinoxaline-fused benzo[h]isoxazolo[5,4-b]quinoline analogues by treating with benzene-1,2-diamine under microwave irradiation. The structural assignment has been ambiguously confirmed by X-ray analysis. A new mechanism has been proposed for this new multicomponent domino process.

Original languageEnglish
Pages (from-to)3834-3838
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number10
DOIs
StatePublished - May 21 2011

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