Formation of isoxazole derivatives via nitrile oxide using ammonium cerium nitrate (CAN): a novel one-pot synthesis of 3-acetyl- and 3-benzoylisoxazole derivatives

被引：52

作者：

Itoh, K ^{[1
]}

Horiuchi, CA ^{[1
]}

机构：

[1] Rikkyo Univ, Dept Chem, Toshima Ku, Tokyo 1718501, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 07期

关键词：

ammonium cerium(IV) nitrate; ammonium cerium(III) nitrate; formic acid; isoxazole derivatives; nitrile oxide;

D O I：

10.1016/j.tet.2003.11.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of alkenes and alkynes with ammonium cerium(IV) nitrate ((NH4)(2)CC(NO3)(6), CAN(IV)) in acetone under reflux gave the corresponding 3-acetyl-4,5-dihydroisoxazole and 3-acetylisoxazole derivatives. In the case of acetophenone, 3-benzoyl-4,5-dihydroisoxazole and 3-benzoylisoxazole derivatives were obtained. Reaction of acetone with CAN(IV) afforded the corresponding furoxan (3,4-diacetyl-1,2,5-oxadiazole 2-oxide) as the dimer of nitrile oxide. Moreover, it was found that yields of isoxazole derivatives were improved using ammonium cerium(III) nitrate tetrahydrate ((NH4)(2)Ce(NO3)(5)-4H(2)O, CAN(III))-formic acid. The reaction mechanisms based on nitration and formation of nitrile oxide mediated by CAN(IV) or CAN(III) from acetone or acetophenone are also proposed. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：1671 / 1681

页数：11

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