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Chapter 5.7 Five-membered ring systems: With O&N atoms

Elsevier B.V.
DOI: 10.1016/s0959-6380(03)80014-4


Publisher Summary This chapter describes five-membered ring systems containing oxygen and nitrogen. The interest in this heterocyclic system is still growing and from a synthetic viewpoint significant improvements have been obtained through the applications of new techniques to classic synthetic approaches. In particular, 1,3-dipolar cycloadditions (1,3-DC) of nitrile oxides continue to be one of the main strategies for the synthesis of isoxazoles and isoxazolines and the first soluble polymer-supported synthesis of structurally different derivatives has been described. A soluble poly(ethylene glycol) (PEG)-supported alkyne was allowed to react with nitrile oxides, generated in situ from chlorooximes, affording isoxazoles in good yield and purity after cleavage from the resin.

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