A facile synthesis of spiroisoxazolines: Intramolecular cyclization of 3-aryl-2-nitroacrylates promoted by titanium tetrachloride

被引：14

作者：

Hirotani, S ^{[1
]}

Kaji, E ^{[1
]}

机构：

[1] Kitasato Univ, Sch Pharmaceut Sci, Minato Ku, Tokyo 1088641, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 14期

关键词：

titanium tetrachloride; intramolecular cyclization; nitroacrylates; spiroisoxazolines;

D O I：

10.1016/S0040-4020(99)00119-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Titanium tetrachloride-induced cyclization of 3-(o- or m-substituted p-methoxyphenyl)-2-nitro acrylates (1) provided stereoselectively (4 alpha,5 beta)-1-oxa-2-azaspiro[4, 5]deca-2,6,9-trien-8-ones (2). Ortho-substituted p-methoxyphenyl nitroacrylates gave 2 in good yield. 3-(4'-methoxy-1'-naphthyl)-2-nitroacrylate also reacted with titanium tetrachloride to give quantitatively (4 alpha,5 beta)-4'-oxospiro[isoxazole-(4H)5,1'(4'H)-naphthalene]. 3-(10'-methoxy-9'-anthryl)-2-nitroacrylate was converted to 10-oxospiro-[anthracene-(10H)9,5'(4'H)-isoxazole]. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4255 / 4270

页数：16

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