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Note | Regular issue | Vol 60, No. 7, 2003, pp.1625-1631
Published online, 28th April, 2003
DOI: 10.3987/COM-03-9763
Reductive Cleavage of Fused Isoxazoles with Chlorotrimethylsilane/Sodium Iodide: A Convenient Route to 3,4-Disubstituted Isoxazoles

Hyung Jin Kim,* Kyung Ho Choi, and Kwang-Jin Hwang

*Department of Applied Chemistry, Chonnam National Unviersity, Kwangju, 500-757, Korea

Abstract

The reaction of 7-aryl-4,5-dihydro-7H-pyrano- and 6-aryl-4H,6H-furo[3,4-c]isoxazoles with a combination of TMSCl/NaI afforded reductively ring cleaved 3,4-disubstituted isoxazoles (3, 4, 6 and 7). TMSCl/NaI (5/10 equivalents) mediated reductive cleavage of 3,6-disubstituted 4H,6H-furo[3,4-c]isoxazole (5) efficiently provided the key intermediates (6) and (7) leading to new fused isoxazoles, 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine (8,9) via further synthetic modification.