Scientia Iranica

Scientia Iranica

Solvent-free synthesis of -benzylpyrano[3,2-c]pyran/chromene-2,5-diones via tandem reaction of 4-hydroxy-6-methyl-pyran-2-one and 4-hydroxycoumarin with Baylis-Hillman adduct acetates

Authors
F. Matloubi Moghaddam 1
B. Koushki Foroushani 2
E. Lotfi Kalahroodi 1
1 Laboratory of Organic Synthesis and Natural Products, Department of Chemistry, Sharif University of Technology, Tehran, P. O. Box: 11155-9516, Iran
2 Laboratory of Organic Synthesis and Natural Products, Department of Chemistry, Sharif University of Technology, Tehran, P. O. Box: 11155-9516, Iran.
Abstract
4-hydroxycoumarin 2a and 4-hydroxy-6-methyl-pyran-2-one 2b were applied in a one-pot reaction with Baylis-Hillman adduct acetates 1 to form novel 3-benzylpyrano [3, 2-c] pyran-2, 5-diones 3 in high yields (70-85%). The synthesized framework isavailable in many biologically active moieties. The reaction was carried out under di erent conditions to achieve optimum conditions. The results indicated that Et3N, as a base under solvent-free conditions, was optimum. The reaction procedure and puri cation method are mild and straightforward.
Keywords
Baylis-Hilman adduct acetate
4-hydroxycoumarin
Annulated 2-pyrone
solvent-free conditions
Scientia Iranica
Volume 21, Issue 3
Transactions on Chemistry and Chemical Engineering (C)
June 2014
Pages 735-741

  • Receive Date 01 July 2014
  • Accept Date 27 July 2017