Photochemical and Thermal Bergman Cyclization of a Pyrimidine Enediynol and Enediynone

Nakyen Choy, Beatriz Blanco, Jenghai Wen, Awtar Krishan, K. C. Russell

Research output: Contribution to journalArticlepeer-review

72 Scopus citations

Abstract

formula presented Novel 10-membered pyrimidine enediynes (3 and 4) were synthesized in seven and eight steps, respectively. These compounds were compared for their abilities to undergo Bergman cyclization both thermally and photochemically. Alcohol 3 readily cyclized both thermally and photochemically in iPrOH, while ketone 4 only showed efficient thermal cyclization. Both compounds were also shown to cleave dsDNA under the appropriate conditions.

Original languageEnglish (US)
Pages (from-to)3761-3764
Number of pages4
JournalOrganic letters
Volume2
Issue number24
DOIs
StatePublished - Nov 30 2000

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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