Cyanuric chloride catalyzed mild protocol for synthesis of biologically active dihydro/spiro quinazolinones and quinazolinone-glycoconjugates

J Org Chem. 2012 Jan 20;77(2):929-37. doi: 10.1021/jo2020856. Epub 2012 Jan 9.

Abstract

We have developed an efficient cyanuric chloride (2,4,6-trichloro-1,3,5-triazine, TCT) catalyzed approach for the synthesis of 2,3-dihydroquinazolin-4(1H)-one (3a-3x), 2-spiroquinazolinone (5, 7), and glycoconjugates of 2,3-dihydroquinazolin-4(1H)-one (10a, 10b) derivatives. The reaction allows rapid cyclization (8-20 min) with 10 mol % cyanuric chloride to give skeletal complexity in good to excellent yield. We believe that this novel procedure may open the door for the easy generation of new and bioactive quinazolinones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Glycoconjugates / chemical synthesis*
  • Glycoconjugates / chemistry
  • Imines / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Quinazolinones / chemical synthesis*
  • Quinazolinones / chemistry
  • Triazines / chemistry*
  • ortho-Aminobenzoates

Substances

  • Glycoconjugates
  • Imines
  • Quinazolinones
  • Triazines
  • ortho-Aminobenzoates
  • cyanuric chloride
  • anthranilamide