Switching Regioselectivity of β-Ketothioamides by Means of Iodine Catalysis: Synthesis of Thiazolylidenes and 1,4-Dithiines

An efficient I2‐catalyzed synthesis of thiazolylidenes and 1,4‐dithiines from β‐ketothioamides (KTAs) has been developed by only controlling the amount of I2 that triggers different cascade reaction sequences by means of [3+2] or [3+3] cyclocondensation in a one‐step process. A possible mechanistic...

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Veröffentlicht in:Chemistry : a European journal 2014-04, Vol.20 (17), p.5028-5033
Hauptverfasser: Wen, Li-Rong, Men, Lian-Bin, He, Tao, Ji, Guo-Jing, Li, Ming
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Sprache:eng
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Zusammenfassung:An efficient I2‐catalyzed synthesis of thiazolylidenes and 1,4‐dithiines from β‐ketothioamides (KTAs) has been developed by only controlling the amount of I2 that triggers different cascade reaction sequences by means of [3+2] or [3+3] cyclocondensation in a one‐step process. A possible mechanistic proposal for these transformations is presented. In control: An efficient I2‐catalyzed synthesis of thiazolylidenes and 1,4‐dithiines from β‐ketothioamides has been developed by controlling the amount of I2, which triggers different cascade reaction sequences through [3+2] or [3+3] cyclocondensation in a one‐step process (see scheme). A possible mechanistic proposal for these transformations is presented (DABCO=1,4‐diazabicyclo[2⋅2⋅2]octane).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201304497