Unusual product distribution from Friedländer reaction of di- and triacetylbenzenes with 3-aminonaphthalene-3-carbaldehyde and properties of new benzo[g]quinoline-derived aza-aromatics

Molecules. 2014 Aug 21;19(8):12842-51. doi: 10.3390/molecules190812842.

Abstract

The Friedländer reactions of acetylbenzenes and 2-acetylpyridine with 3-aminonaphthalene-2-carbaldehyde afforded the corresponding 2-phenylbenzo[g]quinoline and 2-(pyrid-2-yl)benzo[g]quinoline, respectively. The same reactions of 3-aminonaphthalene-2-carbaldehyde with 1,2-, 1,3-, 1,4-di- and 1,3,5-triacetylbenzenes, however, afforded a series of corresponding (benzo[g]quinolin-2-yl)benzenes as new N,C-bidentate and unexpected benzo[g]quinoline. Crystallinity, thermal properties, absorption and emission spectral properties of the products were studied.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Benzene Derivatives / chemistry*
  • Calorimetry, Differential Scanning
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Naphthalenes / chemistry*
  • Powder Diffraction
  • Quinolines / chemistry*
  • X-Ray Diffraction

Substances

  • 3-aminonaphthalene-3-carbaldehyde
  • Aldehydes
  • Benzene Derivatives
  • Heterocyclic Compounds, 4 or More Rings
  • Naphthalenes
  • Quinolines