Beilstein Journal of Organic Chemistry p. 2739 - 2750 (2017)
Update date:2022-08-24
Topics:
Roslan, Irwan Iskandar
Ng, Kian-Hong
Chuah, Gaik-Khuan
Jaenicke, Stephan
Two regiodivergent approaches to intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and amides have been developed, controlled by the reagents employed. With the Br?nsted base KOt-Bu and CBrCl3 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.
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