STUDIES ON ORGANOSILICON CHEMISTRY .118. SYNTHESIS AND REACTIONS OF METHYL (TRIMETHYLSILYLMETHYL)-ACETYLENECARBOXYLATE - A GENERAL-METHOD FOR THE GENERATION OF DI-EXO-METHYLENEISOXAZOLINES AND NOVEL ACCESS TO FUSED ISOXAZOLES

被引：33

作者：

HOJO, M ^{[1
]}

TOMITA, K ^{[1
]}

HOSOMI, A ^{[1
]}

机构：

[1] UNIV TSUKUBA,DEPT CHEM,TSUKUBA,IBARAKI 305,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 03期

关键词：

METHYL (TRIMETHYLSILYLMETHYL)ACETYLENECARBOXYLATE, 1,3-DIPOLAR CYCLOADDITION; 1,4-ELIMINATION; DI-EXO-METHYLENEISOXAZOLINE; DIELS-ALDER REACTION; FUSED ISOXAZOLE;

D O I：

10.1016/0040-4039(93)85108-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl (trimethylsilylmethyl)acetylenecarboxylate, which is a common key compound in preparation of precursors for di-exo-methylene derivatives of isoxazolines, reacts with nitrile oxides to yield cycloadducts, isoxazoles. Reduction and acetylation of cycloadducts leading to 4-acetoxymethyl-5-(trimethylsilylmethyl)isoxazoles followed by fluoride ion-promoted 1,4-elimination reaction in the presence of dienophiles gave fused isoxazoles.

引用

页码：485 / 488

页数：4

共 10 条

[1] CALDIROLA P, 1985, HETEROCYCLES, V23, P2479
[2] ORTHOQUINODIMETHANES
CHARLTON, JL
ALAUDDIN, MM
[J]. TETRAHEDRON, 1987, 43 (13) : 2873 - 2889
[3] CHEMISTRY OF ORGANOSILICON COMPOUNDS .222. 2-DIMETHYLAMINOMETHYL-3-TRIMETHYLSILYLMETHYL-1,3-BUTADIENE AS 2,2'-BIALLYL DIRADICAL SYNTHON - A NEW AND FACILE ENTRY TO 1,2-DIMETHYLENECYCLOHEXANES, AND [6.6] AND [6.7] RING-SYSTEMS
HOSOMI, A
OTAKA, K
SAKURAI, H
[J]. TETRAHEDRON LETTERS, 1986, 27 (25) : 2881 - 2884
[4] CHEMISTRY OF ORGANO-SILICON COMPOUNDS .195. "N-(TRIMETHYLSILYLMETHYL)AMINOMETHYL ETHERS AS AZOMETHINE YLIDE SYNTHONS - A NEW AND CONVENIENT ACCESS TO PYRROLIDINE DERIVATIVES
HOSOMI, A
SAKATA, Y
SAKURAI, H
[J]. CHEMISTRY LETTERS, 1984, (07) : 1117 - 1120
[5] CHLOROMETHYL TRIMETHYLSILYLMETHYL SULFIDE AS A PARENT THIOCARBONYL YLIDE SYNTHON - A SIMPLE SYNTHESIS OF DIHYDRO-THIOPHENES AND TETRAHYDRO-THIOPHENES
HOSOMI, A
MATSUYAMA, Y
SAKURAI, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (14) : 1073 - 1074
[6] HOSOMI A, IN PRESS REV HETEROA
[7] GENERATION AND CYCLOADDITION REACTIONS OF THE 1,2,3-TRIAZOLE ANALOG OF ORTHO-QUINODIMETHANE
MERTZANOS, GE
STEPHANIDOUSTEPHANATOU, J
TSOLERIDIS, CA
ALEXANDROU, NE
[J]. TETRAHEDRON LETTERS, 1992, 33 (31) : 4499 - 4502
[8] THE REACTIONS OF PRIMARY NITROPARAFFINS WITH ISOCYANATES
MUKAIYAMA, T
HOSHINO, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (20) : 5339 - 5342
[9] A GENERAL SYNTHESIS OF 4-ISOXAZOLECARBOXYLIC ACIDS
STORK, G
MCMURRY, JE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (21) : 5461 - &
[10] TOMINAGA Y, 1992, YUKI GOSEI KAGAKU KY, V50, P48

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