Access to 4-substituted isothiazoles through three-component cascade annulation and their application in C-H activation

The use of potassium ethyl xanthate (EtOCS 2 k) as a sulfur atom donor enabled the transition-metal-free [3 + 1 + 1] cascade annulation of isopropene derivatives with NH 4 I in DMSO/H 2 O, affording various 4-substituted isothiazoles in moderate to good yields with good functional group compatibilit...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-05, Vol.56 (43), p.5763-5766
Main Authors: Huang, Guoling, Li, Jian, Ji, Xiaoliang, Chen, Lu, Liu, Qiang, Chen, Xiuwen, Huang, Yubing, Li, Yibiao
Format: Article
Language:English
Subjects:
Activation
Chemical reactions
Covalent bonds
Crystallography
Dimerization
Functional groups
NMR
Nuclear magnetic resonance
Organic chemistry
Oxidation
Palladium
Silver
Substitutes
Transition metals
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Summary:The use of potassium ethyl xanthate (EtOCS 2 k) as a sulfur atom donor enabled the transition-metal-free [3 + 1 + 1] cascade annulation of isopropene derivatives with NH 4 I in DMSO/H 2 O, affording various 4-substituted isothiazoles in moderate to good yields with good functional group compatibility. Furthermore, Pd and Ag-catalyzed C5-H-selective direct oxidation dimerization of 4-substituted isothiazoles afforded 5,5′-bisisothiazoles. This series of reactions included the formation of new C-S, C-N, N-S, and C-C bonds via cascade addition, annulation, and direct C-H activation under mild conditions. The use of EtOCS 2 k enabled the annulation of isopropene derivatives with NH 4 I, affording various 4-substituted isothiazoles in good yields.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc01100b