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 KOBu and CBrCl as radical initiator, benzo[]imidazo[2,1-]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), results in the regioselective nucleophilic attack at both carbonyl groups forming benzo[4,5]thiazolo[3,2-]pyrimidin-4-ones instead.
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| http://dx.doi.org/10.3762/bjoc.13.270 | DOI Listing |
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