Cycloaddition reactions of thiazolium azomethine ylides: application to pyrrolo[2,1-b]thiazoles |
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Authors: | Berry Craig R Zificsak Craig A Gibbs Alan C Hlasta Dennis J |
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Institution: | Johnson & Johnson Pharmaceutical Research & Development, L.L.C., 8 Clarke Drive, Cranbury, New Jersey 08512, USA. |
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Abstract: | Thiazolium azomethine ylides, equipped with a C-2 methanethiol group, participate in an efficient 3 + 2] cycloaddition reaction with acetylene derivatives to yield unique pyrrolo2,1-b]thiazoles. The elimination of the methanethiol leaving group from the cycloadduct has replaced the need for a separate oxidation step and suppresses ring-opening side reactions. Products were obtained in short synthetic sequences to demonstrate their use as a scaffold for compound libraries. |
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