Please use this identifier to cite or link to this item: https://doi.org/10.3762/bjoc.13.270
Title: Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with ?-ketoesters and ?-ketoamides
Authors: Roslan, I.I 
Ng, K.-H
Chuah, G.-K 
Jaenicke, S 
Issue Date: 2017
Citation: Roslan, I.I, Ng, K.-H, Chuah, G.-K, Jaenicke, S (2017). Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with ?-ketoesters and ?-ketoamides. Beilstein Journal of Organic Chemistry 13 : 2739-2750. ScholarBank@NUS Repository. https://doi.org/10.3762/bjoc.13.270
Abstract: Two regiodivergent approaches to intermolecular cyclization of 2-aminobenzothiazoles with ?-ketoesters and amides have been developed, controlled by the reagents employed. With the Brønsted base KOt-Bu and CBrCl3 as radical initiator, benzo[d]imidazo[2,1-b]thiazoles are synthesized via attack at the ?-carbon and keto carbon of the ?-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. © 2017 Roslan et al.
Source Title: Beilstein Journal of Organic Chemistry
URI: https://scholarbank.nus.edu.sg/handle/10635/173757
ISSN: 18605397
DOI: 10.3762/bjoc.13.270
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