Synthesis of Isoxazole Conjugates of 1,4-Benzodioxane Moiety via Intermolecular 1,3-Dipolar Cycloaddition

Abstract

1,3-Dipolar cycloaddition was utilized as a tool to conjugate the 1,4-benzodioxane moiety with several biologically active compounds such as steroid, sugar, and other aromatic scaffolds via isoxazole or triazole bridge. The propynyl ether of 2-hydroxymethyl-1,4-benzodioxane underwent 1,3-dipolar cycloadditions smoothly with different in situ generated nitrile oxides in good yields. The triazole conjugate of 1,4-benzodioxane was synthesized via click chemistry.

Keywords:

• 1,4-Benzodioxane
• click chemistry
• 1,3-dipolar cycloadditions
• isoxazole
• triazole

ACKNOWLEDGMENTS

We thank the University Grants Commission (UGC) and Defence Research and Development Organisation (DRDO), New Delhi, for the financial support. V. V. V. thanks UGC for the award of a fellowship [F-12–25/(2003)].