Journal
MOLECULES
Volume 27, Issue 23, Pages -Publisher
MDPI
DOI: 10.3390/molecules27238426
Keywords
N-arylcyanothioformamides; 4; 5-dichloro-1; 2; 3-dithiazolium chloride; N-arylimino-1; 3-dithiazoles; 2-cyanobenzothiazoles; C-S bond formation
Funding
- European Regional Development Fund (ERDF)
- Labex SynOrg
- Carnot Institute I2C [ANR-11-LABX-0029]
- graduate school for research Xl-Chem
- [ANR-18-EURE-0020 XL CHEM]
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In this study, a catalytic system involving palladium and copper is reported for the cyclization of N-arylcyanothioformamides and the synthesis of 2-cyanobenzothiazoles. The C-H functionalization/intramolecular C-S bond formation reaction was achieved in the presence of air using 2.0 equiv of an inorganic additive (KI). The reaction led to sole product formation in good yields, allowing the synthesis of various substituted 2-cyanobenzothiazole derivatives that can be used as building blocks for the design of more complex heterocyclic or molecular labeling systems.
We report herein on a catalytic system involving palladium and copper to achieve the cyclization of N-arylcyanothioformamides and the synthesis of 2-cyanobenzothiazoles. The C-H functionalization/intramolecular C-S bond formation reaction was achieved in the presence of air, using 2.0 equiv of an inorganic additive (KI). In many cases, the reaction led to a sole product regioselectively obtained in good yields, allowing the synthesis of a wide range of substituted 2-cyanobenzothiazole derivatives, providing valuable building blocks for the design of more complex heterocyclic or molecular labeling systems.
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