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Attempted Synthesis of Carboxin Derivative through Ring Expansion Reaction on Solid Phase  

Hahn, Hoh-Gyu (Organic Chemistry Lab, Korea Institute of Science and Technology)
Bae, Su-Yeal (Organic Chemistry Lab, Korea Institute of Science and Technology)
Nam, Kee-Dal (Organic Chemistry Lab, Korea Institute of Science and Technology)
Publication Information
The Korean Journal of Pesticide Science / v.9, no.3, 2005 , pp. 185-190 More about this Journal
Abstract
Solid phase synthesis of 16, which is a derivative of the first systemic fungicide, carboxin 1 was described. Reaction of 1,3-oxathiolane derivative with solid resin of 4-hydroxy-3-nitrobenzophenone 6 gave 9 in 82% yield. Oxidation of sulfur in the solid 1,3-oxathiolane 9 by MCPBA followed by a ring expansion reaction under the acid catalyst afforded the corresponding dihydro-1,4-oxathiin derivative 12. Treatment of the solid 1,3-oxathiolane 9 with p-methoxyaniline resulted in 1,3-oxathiolane 14, 1,3-oxathiolane sulfoxide 15, dihydro-1,4-oxathiin 16, and acetoacetanilide derivative 17 in 41%, 35%, 14%, 10% yields, respectively.
Keywords
acylation; carboxin; 4-hydroxy-3-nitrobenzophenone; ring expansion reaction; solid phase synthesis;
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