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

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

Scientia Iranica
Volume 21, Issue 3
Transactions on Chemistry and Chemical Engineering (C)
June 2014
Pages 735-741

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History

  • Receive Date: 01 July 2014
  • Revise Date: 22 December 2024
  • Accept Date: 27 July 2017

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