Cycloaddition/ring opening of 3-unsubstituted cyclic nitronates, isoxazoline and 5,6-dihydro-4H-1,2-oxazine N-oxides, as synthetic equivalents of functionalized nitrile oxides

被引：19

作者：

Kanemasa, S ^{[1
]}

Yoshimiya, T

Wada, E

机构：

[1] Kyushu Univ, Inst Adv Mat Study, Kasuga, Fukuoka 816, Japan

[2] Kyushu Univ, Interdisciplinary Grad Sch Engn Sci, Dept Mol Sci & Technol, Kasuga, Fukuoka 8168580, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 48期

关键词：

D O I：

10.1016/S0040-4039(98)01903-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

omega-Halo-alpha-nitropropane and -butane are cyclized with a base to form cyclic nitronates as labile 1,3-dipoles. They can be trapped by a variety of monosubstituted ethenes to give 3-(2-hydroxyethyl)isoxazolines or perhydroisoxazolo[2,3-b]o-oxazines depending upon the ring size of nitronates. The latter ring-fused heterocycles are transformed by treatment with an acid into 3-(3-hydroxypropyl)isoxazolines in good yields. Therefore, these cyclic nitronates are useful synthetic equivalents of functionalized nitrile oxides. Isolation of 5,6-dihydro-4H-1,2-oxazine N-oxide and their regio- and stereoselective cycloadditions are also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8869 / 8872

页数：4

共 18 条

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Lukoyanov, Alexander A.
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SYNTHESIS-STUTTGART, 2010, (03): : 407 - 414
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Malykhin, R. S.
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TETRAHEDRON LETTERS, 2015, 56 (16) : 2102 - 2105
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