Straightforward synthesis of biologically relevant benzothiazole heterocycles

What is it about?

Aminobenzothiazoles, a class of heterocyclic structures present in many bioactive plant metabolites and pharmaceuticals have been eficiently synthesised from simple and readily available starting materials. To achieve this goal common anilines have been subjected to a reaction discovered a century ago by the german chemist Richard Herz and then to a novel insetion reaction with isocyanides. Remarkably, one new carbon-nitrogen and two new cabon-sulfur bonds are formed in this process.

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Why is it important?

Heterocycles are challenging targets for organic synthesis. In this work, thiazole (a heterocyle containing carbon, nitrogen and sulfur atoms) is built from three different types of starting materials, each providing a different element. The importance of this strategy lies, not only in its experimental simplicity, but also in the diversity of products attainable from different combination of the three starting reactants.