Reactions of Benzothiazoles

Reactions of Benzothiazoles

While the parent compound, benzothiazole, is not extensively utilized, numerous of its derivatives can be found in commercial products or occur naturally.

Reacion-1:

Both oxygen and sulfur substituents in benzothiazoles can be readily replaced by organolithiums or amines.

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Reacion-2:

Benzothiazoles (with nitrogen protection or blocking) undergo lithiation at the 2-position of the hetero-ring, enabling subsequent reactions with the typical array of electrophiles, as demonstrated in the following examples where a silicon substituent is introduced.

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Reacion-3:

K2S2O8 facilitates a non-transition metal-catalyzed synthesis of 2-aryl benzothiazoles via the oxidative condensation of benzothiazoles with aryl aldehydes or phenylglyoxylic acids.

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See also:

References:

[1]Wu Y J. Thiazoles and Benzothiazoles[J]. Metalation of Azoles and Related Five-Membered Ring Heterocycles, 2012: 307-327.

[2]Ranjit S, Liu X. Direct arylation of benzothiazoles and benzoxazoles with aryl boronic acids[J]. Chemistry–A European Journal, 2011, 17(4): 1105-1108.