Synlett 2015; 26(14): 1985-1990
DOI: 10.1055/s-0034-1378783
letter
© Georg Thieme Verlag Stuttgart · New York

Facile Synthesis of Benzo[d]azol-2(3H)-ones Using 2-Phenoxycarbonyl-4,5-dichloropyridazin-3(2H)-one as Green CO Source

Ki Eun Ryu
a   Department of Chemistry & Research Institute of Natural Science, Gyeongsang National University, Jinju, 660-701, South Korea   eMail: yjyoon@gnu.ac.kr
,
Bo Ram Kim
a   Department of Chemistry & Research Institute of Natural Science, Gyeongsang National University, Jinju, 660-701, South Korea   eMail: yjyoon@gnu.ac.kr
,
Gi Hyeon Sung
a   Department of Chemistry & Research Institute of Natural Science, Gyeongsang National University, Jinju, 660-701, South Korea   eMail: yjyoon@gnu.ac.kr
,
Hyo Jae Yoon*
b   Department of Chemistry, Korea University, Seoul, 136-701, South Korea   eMail: hyoon@korea.ac.kr
,
Yong-Jin Yoon*
a   Department of Chemistry & Research Institute of Natural Science, Gyeongsang National University, Jinju, 660-701, South Korea   eMail: yjyoon@gnu.ac.kr
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Publikationsverlauf

Received: 01. Mai 2015

Accepted after revision: 12. Juni 2015

Publikationsdatum:
23. Juli 2015 (online)


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Abstract

Developing eco-friendly, stable, and easy-to-handle acyl sources is of great importance in synthetic and green chemistry. This study describes the synthesis of benzo[d]azol-2(3H)-ones such as benzo[d]thiazol-2(3H)-ones, benzo[d]oxazol-2(3H)-ones, and benzo[d]imidazol-2(3H)-ones using 2-phenoxycarbonyl-4,5-dichloropyridazin-3(2H)-one in one pot. The reaction reported is carried out under neutral or acidic conditions in the presence of zinc or sodium bicarbonate to give the corresponding heterocycles in good to excellent yields. The reaction uses a solid stable carbonyl source that is a recyclable functional-group carrier, pyridazin-3(2H)-one.

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