Alkyl and aryl 4,5-dichloro-6-oxopyridazin-1(6 H)-carboxylates: A practical alternative to chloroformates for the synthesis of symmetric and asymmetric carbonates

Hyun Kyung Moon, Gi Hyeon Sung, Yong Jin Yoon, Hyo Jae Yoon

Research output: Contribution to journalArticlepeer-review

Abstract

Symmetric and asymmetric carbonates were synthesized by using alkyl or aryl 4,5-dichloro-6-oxopyridazin-1(6H)-carboxylates. Five aryl 4,5-dichloro-6-oxopyridazin-1(6H)-carboxylates were converted into the corresponding diaryl carbonates in good to excellent yields by treatment with potassium carbonate in refluxing THF. When the 4,5-dichloro-6-oxopyridazin-1(6H)-carboxylates were treated with aliphatic or aromatic alcohols in the presence of potassium tert-butoxide in toluene at room temperature, they gave the corresponding symmetric or asymmetric carbonates in moderate to excellent yields. Alkyl and aryl 4,5-dichloro-6-oxopyridazin-1(6H)-carboxylates are therefore efficient, stable, and ecofriendly alternatives to chloroformates.

Original languageEnglish
Article numberst-2016-u0006-l
Pages (from-to)1577-1581
Number of pages5
JournalSynlett
Volume27
Issue number10
DOIs
Publication statusPublished - 2016 Jun 2

Keywords

  • acyl-transfer agents
  • alcohols
  • alkoxycarbonylations
  • carbonates
  • phenols
  • pyridazines

ASJC Scopus subject areas

  • Organic Chemistry

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