An Efficient Synthesis of Oxygen-Bridged Spirooxindoles via Microwave-Promoted Multicomponent Reaction

Abstract

A microwave-promoted multicomponent reaction of isatins, α-amino acids and 1,4-dihydro-1,4-epoxynaphthalene is achieved under environmentally friendly conditions, delivering oxygen-bridged spirooxindoles within 15 min in good to excellent yields. The attractive features of the 1,3-dipolar cycloaddition are the compatibility of various primary amino acids and the high efficiency of the short reaction time. Moreover, the scale-up reaction and synthetic transformations of spiropyrrolidine oxindole further demonstrate its synthetic utility. This work provides powerful means to expand the structural diversity of spirooxindole as a promising scaffold for novel drug discovery.

Keywords

• green chemistry
• microwave
• multicomponent reaction
• [3+2] cycloaddition
• oxygen-bridged spirooxindoles