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Thiazoles

This chapter is a review of the scientific literature from 1995 to 2007. In conjunction with the corresponding chapters in CHEC(1984) and CHEC-II(1996), it constitutes a thorough review of the chemistry of thiazoles. Structures discussed include thiazoles, thiazolines, thiazolidines, thiazolium salts, benzothiazoles, and benzothiazolines as well as more complex structures and/or fused systems bearing substituents on the ring carbons and heteroatoms. The chapter’s subsections describe theoretical methods (including molecular orbital calculations, bond lengths and angles, electronic density and aromaticity), experimental measurements (covering various techniques such as X-ray diffraction, and IR and UV spectroscopies, mass spectrometry, and NMR spectroscopy), a survey of the reactivity of thiazole systems (covering reactivity of the ring carbons, heteratoms, and attached functional groups), approaches to ring synthesis (organized by the number of atoms in each component used), a comparison of the various routes to classes of compounds containing thiazoles (including biosynthesis and solid-phase approaches), and important thiazole compounds and their applications (including naturally occurring thiazole systems, thiazole peptides, lactones and alkaloids, and synthetic tools such as thiazole as a formyl equivalent, thiazolidine thiones as chiral auxiliaries, and thiazolium catalysts). Other applications of thiazoles such as fluorescence PNA probes for DNA determination, synthetic fluorophores, and DNA nucleases are also discussed.

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