Solid-Phase Syntheses of Heterocycles Containing the 2-Aminothiophenol Moiety1
作者： T. Scott Yokum , Jordi Alsina , George Barany
DOI: 10.1021/CC9900854
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摘要: Efficient and general procedures have been developed for the solid-phase preparation of substituted benzothiazoles (1), 3,4-dihydro-1,4-benzothiazines (2), 3,4-dihydro-1,4-benzothiazine-1,1-dioxides (3), 3,4-dihydro-3-oxo-1,4-benzothiazines (4), 3,4-dihydro-3-oxo-1,4-benzothiazine-1,1-dioxides (5). All five classes compounds were prepared from a common intermediate, resin-bound 2-amino-4-carboxythiophenol, in minimal number steps. This intermediate was generated by (i) coupling 4-fluoro-3-nitrobenzoic acid onto Wang resin, or an amino bound to (ii) substitution aryl fluoride with protected thiol, (iii) reduction nitro group, (iv) removal sulfur protection. Reaction appropriate substrates reagents effect cyclization gave core structures, which modified further introduce additional point(s) diversity. Following cleavages solid support, obtained high initial purities good isol...
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