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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.

SUBMITTER: Shi Y

PROVIDER: S-EPMC10146779 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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

Shi Yaojing Y Zhao Hua H Zhao Yufen Y

Molecules (Basel, Switzerland) 20230416 8

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 ...[more]

PMID: 37110742

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