4-Bromo-2,3-dihydroisoxazoles: synthesis and application in halogen-lithium exchange reactions

Add time:07/15/2019    Source:sciencedirect.com

The synthesis of novel types of 4-bromo-2,3-dihydroisoxazoles using pyridinium tribromide in the presence of base is described. Reactivity of the initial substrates and the yields depend on the substituent at C3. To demonstrate a practical scope of the 4-bromo-substituted 2,3-dihydroisoxazoles, representative 2-benzyl-4-bromo-3,5-diphenyl-2,3-dihydroisoxazole is subjected to halogen-lithium exchange reaction. The corresponding (2,3-dihydroisoxazol-4-yl)lithium reacts with three selected electrophiles to afford 4-substituted 2,3-dihydroisoxazoles in moderate yields.

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