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Two regiodivergent approaches to intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and amides have been developed, controlled by the reagents employed. With the Brønsted base KO t- Bu and CBrCl 3 as radical initiator, benzo[ d ]imidazo[2,1- b ]thiazoles are synthesized via attack at the α-carbon and keto carbon of the β-ketoester moiety. In contrast, switching to the Lewis acid catalyst, In(OTf) 3 , results in the regioselective nucleophilic attack at both carbonyl groups forming benzo[4,5]thiazolo[3,2- a ]pyrimidin-4-ones instead.

Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and β-ketoamides