An efficient I2/K2S2O8-promoted ring expansion of benzo[d]thiazole and 3-oxo-3-arylpropanenitrile has been developed. A variety of benzo[d]thiazole derivatives underwent the ring-opening cyclization smoothly to afford the diverse 3-aryl-4H-benzo[b][1,4]thiazine-2-carbonitriles in moderate to excellent yields. This protocol features metal-free reaction conditions, stable and available starting materials, and good group tolerance. The synthetic utility of this protocol was also demonstrated through gram-scale reaction and product derivatization. Mechanism studies indicate that the reaction may undergo a free radical process.
I2/K2S2O8-Promoted ring-opening cyclizations of benzothiazoles and 3-oxo-3-arylpropanenitriles
Vaccaro L.;
2022
Abstract
An efficient I2/K2S2O8-promoted ring expansion of benzo[d]thiazole and 3-oxo-3-arylpropanenitrile has been developed. A variety of benzo[d]thiazole derivatives underwent the ring-opening cyclization smoothly to afford the diverse 3-aryl-4H-benzo[b][1,4]thiazine-2-carbonitriles in moderate to excellent yields. This protocol features metal-free reaction conditions, stable and available starting materials, and good group tolerance. The synthetic utility of this protocol was also demonstrated through gram-scale reaction and product derivatization. Mechanism studies indicate that the reaction may undergo a free radical process.File in questo prodotto:
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