An efficient one-pot synthesis of 3-aryl-5-methylisoxazoles from aryl aldehydes
S Zhu, S Shi, SW Gerritz
Index: Zhu, Shirong; Shi, Shuhao; Gerritz, Samuel W. Tetrahedron Letters, 2011 , vol. 52, # 31 p. 4001 - 4004
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Citation Number: 15
Abstract
A frequently-cited and robust synthetic route to 3-aryl-5-methylisoxazole carboxylates is the 1,3-dipolar cycloaddition of alkenes and alkynes with nitrile oxides. 5b This procedure involves three discrete steps: (1) conversion of an aldehyde to the corresponding oxime; (2) α-chlorination of the oxime using N-chlorosuccinimide (NCS), usually initiated by HCl gas; and (3) reaction of the resulting hydroximinoyl chloride with a dipolarophile such as an alkyne, 6 the ...
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