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.
An expedient method for the synthesis of glyco-dispiropyrrolidines is reported through 1,3-dipolar cycloaddition reaction (1,3 DC reaction). The novel glycosyl dipolarophiles derived from D-glucose underwent neat [3+2] cycloaddition reaction with the azomethine ylides generated from 1,2-diketones and sarcosine to give the corresponding glycosidic heterocycles in good yields.
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