A novel rearrangement process involving the migration of trimethylstannanyl or trimethylsilanyl groups around the thiazole ring provides access to either 2- or 5-metallated thiazoles by tuning the reaction conditions. The proposed mechanism, based on experimental evidence, is characterized by the catalytic role of thiazole bisadducts as metal-transfer agents. © 2007 Elsevier Ltd. All rights reserved.
Efficient access to 5-substituted thiazoles by a novel metallotropic rearrangement / Zambon, Alfonso; Borsato, Giuseppe; Brussolo, Stefania; Frascella, Pietrogiulio; Lucchini, Vittorio. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 49:1(2008), pp. 66-69. [10.1016/j.tetlet.2007.11.029]
Efficient access to 5-substituted thiazoles by a novel metallotropic rearrangement
ZAMBON, Alfonso;
2008
Abstract
A novel rearrangement process involving the migration of trimethylstannanyl or trimethylsilanyl groups around the thiazole ring provides access to either 2- or 5-metallated thiazoles by tuning the reaction conditions. The proposed mechanism, based on experimental evidence, is characterized by the catalytic role of thiazole bisadducts as metal-transfer agents. © 2007 Elsevier Ltd. All rights reserved.
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