Facile and One-Pot Synthesis of 1,2-Dihydroquinazolin-4(3H)-ones via Tandem Intramolecular Pinner/Dimroth Rearrangement

Abstract

An efficient synthetic method for the preparation of quinazolin-4-one derivatives was designed. The facile condensation of aromatic o-aminonitriles with aromatic aldehydes catalyzed by Lewis acid give 1,2-dihydroquinazolin-4(3H)-ones in moderate to good yields under refluxing dimethylformamide.

Keywords:

• Aromatic aldehyde
• aromatic o-aminonitrile
• catalyst
• cyclocondensation
• one-pot synthesis

ACKNOWLEDGMENTS

This work was supported by grants from both Beijing Municipal Commission of Education and Beijing Institute of Technology. We are grateful for analytical help from Beijing University Analysis Center and Institute of Chemistry, Chinese Academy of Sciences.

Notes

^a All reactions were carried out using 1 (2.5 mmol), 2 (3.0 mmol), ZnCl₂(3.0 mmol), and DMF (3 mL).

^b Isolated yield.