Concise synthesis of 2-amino-4(3H)-quinazolinones from simple (Hetero)aromatic amines

J Org Chem. 2008 Mar 21;73(6):2473-5. doi: 10.1021/jo7026883. Epub 2008 Feb 22.

Abstract

A novel and simple method of preparation of 2-alkylaminoquinazolin-4-ones with fused heteroaromatic rings from easily accessible (hetero)aromatic amines is described. The method is very efficient, and the 2-alkylaminoquinazolinone derivatives are obtained in three steps without chromatographic purification. The key step is the ring closure of the N-protected guanidine intermediates by intramolecular Friedel-Craft's type substitution.

MeSH terms

  • Aniline Compounds / chemistry*
  • Quinazolinones / chemical synthesis*

Substances

  • Aniline Compounds
  • Quinazolinones