Highly Efficient Construction of Sugar-Fused Spirochromanono Pyrrolidines/Pyrrolizidines/Thiolizidines via 1,3-Dipolar Cycloaddition of Azomethine Ylides

Abstract

Abstract A variety of sugar-fused chromanono pyrrolidines/pyrrolizidines/thiolizidines have been synthesized by intermolecular 1,3-dipolar cycloaddition reaction of azomethine ylides (generated from glucose aldehyde and different secondary amino acids) with various 3-arylidene chroman-4-ones as dipolarophiles. The solvent effect on the 1,3-dipolar cycloaddition reaction is also studied.

Keywords

• 1,3-dipolar cycloaddition
• spirochromanones
• glycosyl heterocycles­
• azomethine ylide
• pyrrolidines