One-pot synthesis of simple alkaloids: 2,3-polymethylene-4(3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine

Chem Pharm Bull (Tokyo). 2008 Apr;56(4):607-9. doi: 10.1248/cpb.56.607.

Abstract

One-pot synthesis of various 2,3-polymethylene-4(3H)-quinazolinones from anthranilic acid, corresponding lactam and SOCl(2) is described, which can be applicable to the synthesis of simple 4(3H)-quinazolinone-derived alkaloids, such as luotonin A, tryptanthrin, and rutaecarpine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemical Phenomena
  • Chemistry, Physical
  • Indicators and Reagents
  • Indole Alkaloids / chemical synthesis*
  • Lactams / chemical synthesis
  • Magnetic Resonance Spectroscopy
  • Pyrroles / chemical synthesis*
  • Quinazolines / chemical synthesis*
  • Quinazolinones / chemical synthesis*
  • Quinones / chemical synthesis*
  • Spectrophotometry, Infrared
  • ortho-Aminobenzoates / chemistry

Substances

  • Indicators and Reagents
  • Indole Alkaloids
  • Lactams
  • Pyrroles
  • Quinazolines
  • Quinazolinones
  • Quinones
  • luotonin A
  • ortho-Aminobenzoates
  • anthranilic acid
  • tryptanthrine
  • rutecarpine