Synthesis of Spiro[indole-3,3′-pyrrolidine]-2′-(thi)ones

Motohiro Yasui, Haruna Ohbu, Maho Ishikawa, Tatsuhito Yoshida, Norihiko Takeda, Seiya Hirao, Takumi Abe, Masafumi Ueda

Research output: Contribution to journalArticlepeer-review


Spiro[indole-3,3′-pyrrolidine]-2′-ones were synthesized via one-pot chloroformylation-dearomatizing spirocyclization of tryptamine derivatives. Moreover, the “thio” equivalent spiro[indole-3,3′-pyrrolidine]-2′-thiones, for which the synthesis and properties were previously unreported, were synthesized. The procedures are easily implemented, have a broad scope, and are transition-metal-free and cheap. To demonstrate the utility of the synthetic methodology, the spiro[indole-3,3′-pyrrolidine]-2′-ones were converted into heterocyclic scaffolds, such as an optically active spiroindoline and spirooxindole.

Original languageEnglish
Pages (from-to)1093-1106
Number of pages14
JournalJournal of Organic Chemistry
Issue number2
Publication statusPublished - Jan 20 2023

ASJC Scopus subject areas

  • Organic Chemistry


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