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

doi:10.1055/s-0035-1561411

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 journal › Article › peer-review

3 Citations (Scopus)

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 language	English
Article number	st-2016-u0006-l
Pages (from-to)	1577-1581
Number of pages	5
Journal	Synlett
Volume	27
Issue number	10
DOIs	https://doi.org/10.1055/s-0035-1561411
Publication status	Published - 2016 Jun 2

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the NRF of Korea funded by the Ministry of Science, ICT, & Future Planning (NRF-2014R1A1A1002938) and the Ministry of Education (NRF20100020209).

Publisher Copyright:
© Georg Thieme Verlag Stuttgart New York.

Keywords

acyl-transfer agents
alcohols
alkoxycarbonylations
carbonates
phenols
pyridazines

ASJC Scopus subject areas

Organic Chemistry

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title = "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",

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.",

keywords = "acyl-transfer agents, alcohols, alkoxycarbonylations, carbonates, phenols, pyridazines",

author = "Moon, {Hyun Kyung} and Sung, {Gi Hyeon} and Yoon, {Yong Jin} and Yoon, {Hyo Jae}",

note = "Funding Information: This research was supported by the Basic Science Research Program through the NRF of Korea funded by the Ministry of Science, ICT, & Future Planning (NRF-2014R1A1A1002938) and the Ministry of Education (NRF20100020209). Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart New York.",

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AU - Moon, Hyun Kyung

AU - Sung, Gi Hyeon

AU - Yoon, Yong Jin

AU - Yoon, Hyo Jae

N1 - Funding Information: This research was supported by the Basic Science Research Program through the NRF of Korea funded by the Ministry of Science, ICT, & Future Planning (NRF-2014R1A1A1002938) and the Ministry of Education (NRF20100020209). Publisher Copyright: © Georg Thieme Verlag Stuttgart New York.

PY - 2016/6/2

Y1 - 2016/6/2

N2 - 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.

AB - 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.

KW - acyl-transfer agents

KW - alcohols

KW - alkoxycarbonylations

KW - carbonates

KW - phenols

KW - pyridazines

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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

Abstract

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Keywords

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