Molecular Iodine: An Efficient and Environment Friendly Catalyst for the Synthesis of 3,5-Bis-(arylmethylidene)-tetrahydropyran-4-ones

Abstract

A rapid, efficient, convenient and cost-effective procedure has been developed for the synthesis of 3,5-bis-(arylmethylidene)-tetrahydropyran-4-ones by the condensation of tetrahydropyran-4-one with araldehydes in the presence of catalytic amount of iodine to obtain the products in good to excellent yield. The reactions work at 25 °C and go to completion within 30–60 min.

Keywords:

• Araldehydes
• 3,5-bis-(arylmethylidene)-tetrahydropyran-4-ones
• iodine
• tetrahydropyran-4-one

ACKNOWLEDGMENT

One of the authors, M. B. M. R., wishes to thank Mr. Manjunath, K. Mathematics teacher, St. Claret School, Jalahalli Village, Bengaluru-560013, Karnataka, India, for constant encouragement.

Notes

^a All the products are known and are characterized by IR (entries 3a–3h), ¹HNMR (entries 3a–3d and 3g), LC-mass (entries 3a–3d) spectral analysis from Mp's (entries 3a–3h) and comparison with the samples prepared by reported method [Ref 5].

^b Isolated yields.