A New Approach to Prepare Benzothiazoles
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Abstract:
Benzothiazole derivatives have been drawing great attention due to their antimalarial and antitumor properties.We reported a new approach to prepare benzothiazoles: condensation of thioethylbenzoate with 2-aminothiophenols.The operation is convenient and the reaction proceeds in mild condition.Six compounds in good yields were synthesized by this method.Keywords:
Benzothiazole
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Substituted 2-aminophenyl benzothiazoles have been constructed from thiourea via copper-catalyzed desulfurization/nucleophilic substitution followed by domino intra- and intermolecular C–N cross-coupling reactions under moderate reaction conditions.
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Unexpected Formation of Benzothiazoles in the Synthesis of New Heterocycles: Benzo-1,2,4-dithiazines
The synthesis of benzo-1,2,4-dithiazines was investigated presuming a reversible sulfur-sulfur bond formation. 2-Aminothiophenol, when allowed to react with isothiocyanates, provided benzothiazoles. 2,2′-Diaminodiphenyl disulfide underwent cyclizations very readily without any reducing agent to give, according to the reaction conditions, benzothiazoles or benzo-1,2,4-dithiazines. The developed procedure offers a simple and convenient way to prepare the title compounds in very good to excellent yields. Until now, benzo-1,2,4-dithiazines as well as 2,2′-diaminodiphenyl disulfides bearing aminocarbonothioyl groups were unknown.
Reaction conditions
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An efficient, catalyst free mechanochemical route to 2-aryl benzothiazoles and both 2- and 1,2-disubstituted benzimidazoles has been developed via a simple mortar–pestle grinding method.
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Abstract Thioamides condense with 2-aminothiophenols under convenient and mild conditions to provide a variety of simple and functionalized benzothiazoles in fair to good yields.
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Abstract The convenient procedure allows the preparation of various title compounds in good yields.
Component (thermodynamics)
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A metal-free and operationally simple protocol for the synthesis of structurally diverse 2-hetarylbenzothiazoles via oxidative condensation of the sp3 C–H bond with benzothiazoles has been described.
Benzothiazole
Condensation reaction
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