Chapter 5.5 Five-membered ring systems: With N&S (Se) atoms

Add time:07/13/2019    Source:sciencedirect.com

Publisher SummaryThis chapter discusses the five-membered ring systems with N and S (Se) atoms. The reaction of zirconium metallacycles is used to produce a variety of main group heterocycles through the metallacycle transfer of a carbon fragment. The scope and potential of this reaction for the synthesis of some different heterocycles, including heterocycles containing two heteroatoms, are described in the chapter. In the experiment described in the chapter, the treatment of aryl and heteroaryl o-azidocarbaldehydes with bis(trimethylsilyl)sulfide and hydrochloric acid gave fused isothiazoles through thionation of the formyl function followed by spontaneous decomposition at room temperature. Yield is dependent upon the nature of the heteroaromatic ring. The formation of a carbon–carbon bond in the 4-position of an isothiazole was carried out in moderate yield using the 4-magnesioisothiazole, which was prepared through metal halogen exchange reaction. 4-iodoisothiazole was reacted with ethylmagnesium bromide, then with electrophiles to give ethyl isothiazole-4-carboxylate and isothiazol-4-carbaldehyde. Secondary and tertiary alcohols were obtained from aromatic aldehydes and ketones.

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