Synthesis of 2-Arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones via Rh(2)(OAc)(4)-Catalyzed Reactions of Cyclic 2-Diazo-1,3-diketones with Aryl Isothiocyanates

[Image: see text] A convenient and efficient synthesis of 2-arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones was developed via a Rh(2)(OAc)(4)-catalyzed reaction of cyclic 2-diazo-1,3-diketones and aryl isothiocyanates in acetone at 60 °C. This reaction uses readily available stable cyclic 2-di...

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Autores principales: He, Xinwei, Zhou, Yao, Shang, Yongjia, Yang, Cheng, Zuo, Youpeng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6640800/
https://www.ncbi.nlm.nih.gov/pubmed/31457195
http://dx.doi.org/10.1021/acsomega.6b00295
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author He, Xinwei
Zhou, Yao
Shang, Yongjia
Yang, Cheng
Zuo, Youpeng
author_facet He, Xinwei
Zhou, Yao
Shang, Yongjia
Yang, Cheng
Zuo, Youpeng
author_sort He, Xinwei
collection PubMed
description [Image: see text] A convenient and efficient synthesis of 2-arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones was developed via a Rh(2)(OAc)(4)-catalyzed reaction of cyclic 2-diazo-1,3-diketones and aryl isothiocyanates in acetone at 60 °C. This reaction uses readily available stable cyclic 2-diazo-1,3-diketones as a starting material and generates the desired products in good to excellent yields (78–93%). The reaction proceeds under mild reaction conditions, produces only N(2) as the byproduct, and features a broad substrate scope. A plausible mechanism for this reaction is also discussed.
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spelling pubmed-66408002019-08-27 Synthesis of 2-Arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones via Rh(2)(OAc)(4)-Catalyzed Reactions of Cyclic 2-Diazo-1,3-diketones with Aryl Isothiocyanates He, Xinwei Zhou, Yao Shang, Yongjia Yang, Cheng Zuo, Youpeng ACS Omega [Image: see text] A convenient and efficient synthesis of 2-arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones was developed via a Rh(2)(OAc)(4)-catalyzed reaction of cyclic 2-diazo-1,3-diketones and aryl isothiocyanates in acetone at 60 °C. This reaction uses readily available stable cyclic 2-diazo-1,3-diketones as a starting material and generates the desired products in good to excellent yields (78–93%). The reaction proceeds under mild reaction conditions, produces only N(2) as the byproduct, and features a broad substrate scope. A plausible mechanism for this reaction is also discussed. American Chemical Society 2016-12-19 /pmc/articles/PMC6640800/ /pubmed/31457195 http://dx.doi.org/10.1021/acsomega.6b00295 Text en Copyright © 2016 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle He, Xinwei
Zhou, Yao
Shang, Yongjia
Yang, Cheng
Zuo, Youpeng
Synthesis of 2-Arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones via Rh(2)(OAc)(4)-Catalyzed Reactions of Cyclic 2-Diazo-1,3-diketones with Aryl Isothiocyanates
title Synthesis of 2-Arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones via Rh(2)(OAc)(4)-Catalyzed Reactions of Cyclic 2-Diazo-1,3-diketones with Aryl Isothiocyanates
title_full Synthesis of 2-Arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones via Rh(2)(OAc)(4)-Catalyzed Reactions of Cyclic 2-Diazo-1,3-diketones with Aryl Isothiocyanates
title_fullStr Synthesis of 2-Arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones via Rh(2)(OAc)(4)-Catalyzed Reactions of Cyclic 2-Diazo-1,3-diketones with Aryl Isothiocyanates
title_full_unstemmed Synthesis of 2-Arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones via Rh(2)(OAc)(4)-Catalyzed Reactions of Cyclic 2-Diazo-1,3-diketones with Aryl Isothiocyanates
title_short Synthesis of 2-Arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones via Rh(2)(OAc)(4)-Catalyzed Reactions of Cyclic 2-Diazo-1,3-diketones with Aryl Isothiocyanates
title_sort synthesis of 2-arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5h)-ones via rh(2)(oac)(4)-catalyzed reactions of cyclic 2-diazo-1,3-diketones with aryl isothiocyanates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6640800/
https://www.ncbi.nlm.nih.gov/pubmed/31457195
http://dx.doi.org/10.1021/acsomega.6b00295
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