Effect of Substitution in Stannic Chloride–Mediated Heterocyclization of 4‐Allyl‐3‐hydroxyquinolin‐2(1H)‐ones

Abstract

Effect of substituents at the allylic position in a stannic chloride–iodine–mediated heterocyclization of 4‐allyl‐3‐hydroxyquinolin‐2(1H)‐ones for the regioselective formation of five‐ and six‐membered heterocyclic rings has been rationalized by the application of restricted Hatree–Fock calculation.

Keywords:

• Claisen rearrangement
• 6‐endo‐trig
• 5‐exo‐trig
• Hatree–Fock method
• iodine
• regioselective cyclization
• stannic chloride
• substituent effect

Acknowledgment

We thank the Council of Scientific and Industrial Research (CSIR) (New Delhi) for the financial assistance. N. Kundu is grateful to CSIR (New Delhi) for a junior research fellowship. We also thank Sandip Kar (Bhairab Ganguly College, Belgharia) for his help with the theoretical calculations.