Divergent Synthesis of α‑(1,3,5-Triazinylthio)-ketones and Thiazolo[3,2‑a][1,3,5]triazines from 1,3-Dicarbonyl compounds or Chalcones with 1,3,5-Triazine-2-thiols

Divergent Synthesis of α‑(1,3,5-Triazinylthio)-ketones and Thiazolo[3,2‑a][1,3,5]triazines from 1,3-Dicarbonyl compounds or Chalcones with 1,3,5-Triazine-2-thiols

An efficient synthesis of α-(1,3,5-triazinylthio)-ketones from 1,3-dicarbonyl compounds with 1,3,5-triazine-2-thiols has been developed. The reaction proceeds through the C–C bond cleavage and C–S bond reconstruction of 1,3-dicarbonyl compounds, and β-keto esters, β-keto amides, and 1,3-diones were...

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Veröffentlicht in:Journal of organic chemistry 2023-10, Vol.88 (19), p.14210-14215
Hauptverfasser: Zhong, Pengzhen, Zhang, Cheng, Li, Yue, Su, Chengwu, Zhang, Chen, Cui, Dong-Mei
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container_issue 19
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container_title Journal of organic chemistry
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creator Zhong, Pengzhen
Zhang, Cheng
Li, Yue
Su, Chengwu
Zhang, Chen
Cui, Dong-Mei
description An efficient synthesis of α-(1,3,5-triazinylthio)-ketones from 1,3-dicarbonyl compounds with 1,3,5-triazine-2-thiols has been developed. The reaction proceeds through the C–C bond cleavage and C–S bond reconstruction of 1,3-dicarbonyl compounds, and β-keto esters, β-keto amides, and 1,3-diones were tolerated. In addition, the annulation of 1,3,5-triazine-2-thiols with chalcones has been achieved for the synthesis of thiazolo­[3,2-a]­[1,3,5]­triazines. The method occurred in moderate to good yields and tolerated chalcone with a broad functional group.
doi_str_mv 10.1021/acs.joc.3c01497
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title Divergent Synthesis of α‑(1,3,5-Triazinylthio)-ketones and Thiazolo[3,2‑a][1,3,5]triazines from 1,3-Dicarbonyl compounds or Chalcones with 1,3,5-Triazine-2-thiols
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