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Thiazoles and Benzothiazoles

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Metalation of Azoles and Related Five-Membered Ring Heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 29))

Abstract

This chapter highlights the recent developments in the metalation of thiazoles and benzothiazoles as well as the reactions of the resulting metalated species (2000 to present). Metalation reactions consist of lithiation (including halogen dance reactions), magnesation, zincation, caldation, boronation, and silylation, while application of the metalated thiazoles focuses on nucleophilic additions and metal-catalyzed cross-coupling reactions (Stille, Negishi, and Suzuki). The power of these metalated reactions is amply demonstrated in the total synthesis of the thiazolyl peptide GE2270A.

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Authors and Affiliations

  1. Neuroscience Discovery Chemistry, Research and Development, Bristol-Myers Squibb Company, 5 Research Parkway, Wallingford, CT, 06492, USA

    Yong-Jin Wu

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  1. Yong-Jin Wu
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Correspondence to Yong-Jin Wu .

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Editors and Affiliations

  1. Dept. Chemistry, Dartmouth College, Burke Laboratory 6128, Hanover, 03755, New Hampshire, USA

    Gordon W. Gribble

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© 2012 Springer-Verlag Berlin Heidelberg

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Wu, YJ. (2012). Thiazoles and Benzothiazoles. In: Gribble, G. (eds) Metalation of Azoles and Related Five-Membered Ring Heterocycles. Topics in Heterocyclic Chemistry, vol 29. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2012_78

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