Alkyl and Aryl 4,5-Dichloro-6-oxopyridazin-1(6H)-carboxylates: A Practical Alternative to Chloroformates for the Synthesis of Symmetric and Asymmetric Carbonates
- Authors
- Moon, Hyun Kyung; Sung, Gi Hyeon; Yoon, Yong-Jin; Yoon, Hyo Jae
- Issue Date
- 6월-2016
- Publisher
- GEORG THIEME VERLAG KG
- Keywords
- pyridazines; alcohols; phenols; carbonates; alkoxycarbonylations; acyl-transfer agents
- Citation
- SYNLETT, v.27, no.10, pp.1577 - 1581
- Indexed
- SCIE
SCOPUS
- Journal Title
- SYNLETT
- Volume
- 27
- Number
- 10
- Start Page
- 1577
- End Page
- 1581
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/88452
- DOI
- 10.1055/s-0035-1561411
- ISSN
- 0936-5214
- 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.
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