Multicomponent Dipolar Cycloaddition Strategy: Combinatorial Synthesis of Novel Spiro-Tethered Pyrazolo[3,4-b]quinoline Hybrid Heterocycles

ACS Comb Sci. 2016 May 9;18(5):262-70. doi: 10.1021/acscombsci.6b00003. Epub 2016 Apr 8.

Abstract

The stereoselective syntheses of a library of novel spiro-tethered pyrazolo[3,4-b]quinoline-pyrrolidine/pyrrolothiazole/indolizine-oxindole/acenaphthene hybrid heterocycles have been achieved through the 1,3-dipolar cycloaddition of azomethine ylides generated in situ from α-amino acids and 1,2-diketones to dipolarophiles derived from pyrazolo[3,4-b]quinoline derivatives.

Keywords: 1,3-dipolar cycloaddition; azomethine ylide; isatin; pyrazolo[3,4-b]quinoline; spiro-oxindole; spiro-pyrrolidine; α-amino acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azo Compounds
  • Combinatorial Chemistry Techniques / methods*
  • Cycloaddition Reaction / methods*
  • Heterocyclic Compounds / chemical synthesis*
  • Quinolines / chemical synthesis*
  • Small Molecule Libraries / chemical synthesis
  • Spiro Compounds
  • Stereoisomerism
  • Thiosemicarbazones

Substances

  • Azo Compounds
  • Heterocyclic Compounds
  • Quinolines
  • Small Molecule Libraries
  • Spiro Compounds
  • Thiosemicarbazones
  • azomethine