4.4 Article

Microwave-Assisted One-Pot [3+2] Cycloaddition of Azomethine Ylides and 3-Alkenyl Oxindoles: A Facile Approach to Pyrrolidine-Fused Bis-Spirooxindoles

期刊

CHEMISTRYSELECT
卷 4, 期 5, 页码 1727-1730

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.201802847

关键词

C-C/C-N bond formation; [3+2] Cycloaddition; green protocol; microwave irradiation; pyrrolidine fused-oxindole

资金

  1. DoP, Ministry of Chemicals & Fertilizers, Govt. of India
  2. SERB, DST, Govt. of India [YSS-2015-001709]

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An efficient microwave-assisted one-pot method has been developed for the construction of pyrrolidine fused bis-spirooxindoles through insitu generated azomethine ylide from decarboxylative condensation of isatins and primary alpha-amino acids with concomitant [3+2] cycloaddition of 3-alkenyl oxindoles. These reactions were effectively accelerated by microwave irradiation in ethanol solvent without any additives or catalyst and enable broad substrate scope, atom-economy, eco-friendly, and good yields. The structure and stereochemistry of pyrrolidine fused bis-spirooxindole ring was unambiguously established by single-crystal X-ray analysis.

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