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

Org Biomol Chem. 2011 May 21;9(10):3834-8. doi: 10.1039/c1ob05034f. Epub 2011 Mar 28.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Kinetics
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Quinolines