An efficient synthesis of pyrazolo[3,4-b]quinolin-3-amine and benzo[b][1,8]naphthyridine derivatives

Molecules. 2007 Mar 8;12(3):361-72. doi: 10.3390/12030361.

Abstract

2-Oxo-4-phenyl-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile (10) reacted with hydrazine hydrate, phenylisothiocyanate or benzoyl chloride to give derivatives 12, 13 and 15, respectively. The latter two products were treated with hydrazine hydrate to afford pyrozole[3,4-b]quinolines derivatives 14 and 16, respectively. Compound 10 also reacted with acetonitrile dimer or malononitrile dimer to yield benzo[b][1,8]-naphthyridine derivatives. A single crystal X-ray crystallographic analysis was performed on compound 10, confirming its structure.

MeSH terms

  • Aminoquinolines / chemical synthesis*
  • Aminoquinolines / chemistry
  • Crystallography, X-Ray
  • Naphthyridines / chemical synthesis*
  • Naphthyridines / chemistry
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry

Substances

  • Aminoquinolines
  • Naphthyridines
  • Pyrazoles