Unprecedented one-pot chemocontrolled entry to thioxoimidazolidinones and aminoimidazolones: Synthesis of kinase inhibitor Leucettamine B

Manikandan Selvaraju, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

A novel and highly chemoselective protocol for the construction of thioxoimidazolidinone and aminoimidazolone frameworks was explored, and the influence of the reaction conditions on product formation was studied to establish two distinct approaches for their selective formation. In this one-pot reaction, ambient temperature generally resulted in the formation of thioxoimidazolidinones, whereas microwave irradiation provided aminoimidazolones exclusively. An attempt to elucidate the observed chemoselectivity is described, and the products were confirmed by X-ray studies. One-pot synthesis toward Leucettamine B, a marine alkaloid, was achieved on the basis of this protocol.

Original languageEnglish
Pages (from-to)182-189
Number of pages8
JournalACS Combinatorial Science
Volume17
Issue number3
DOIs
StatePublished - 9 Mar 2015

Keywords

  • chemoselectivity
  • domino reactions
  • microwave chemistry
  • one-pot protocol
  • total synthesis

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