Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement

Nikolai Yu Tiuftiakov, Julia O. Strelnikova, Ilya P. Filippov, Adel R. Khaidarov, Alexander F. Khlebnikov, Alexander S. Bunev, Mikhail S. Novikov, Nikolai V. Rostovskii

Research output: Contribution to journalArticlepeer-review

Abstract

A one-step synthesis of cytotoxic 2-aroylpyrimidines by the denitrogenative reaction of 1-tosyl-1,2,3-triazoles with isoxazoles under rhodium catalysis has been developed. According to the density functional theory calculations and control experiments, the disclosed reaction proceeds via the rearrangement of an oxadiazatetraene intermediate involving a cascade of intramolecular aza-Diels-Alder and retro-aza-Diels-Alder reactions. The presence of a substituent at C4 of the isoxazole is a prerequisite for the formation of the pyrimidines.

Original languageEnglish
Pages (from-to)6998-7002
Number of pages5
JournalOrganic Letters
Volume23
Issue number17
DOIs
StatePublished - 3 Sep 2021

Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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