Efficient synthesis of 4-ethenylidene-2-oxazolidinones via palladium-catalyzed aminocyclization of 2-butyn-1,4-diol biscarbamates

被引：46

作者：

Kimura, M ^{[1
]}

Wakamiya, Y ^{[1
]}

Horino, Y ^{[1
]}

Tamaru, Y ^{[1
]}

机构：

[1] NAGASAKI UNIV,FAC ENGN,DEPT APPL CHEM,NAGASAKI 852,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 22期

关键词：

D O I：

10.1016/S0040-4039(97)00790-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Ethenylidene-2-oxazolidinones 2, 6, and 9 are prepared in reasonable yields by the reaction of 2-butyn-1,4-diol biscarbamates in the presence of catalytic amounts of Pd-2(dba)(3) . CHCl3 (0.005 equiv) ad triethylamine (0.1 equiv). The allenic three carbons are not aligned straight, but considerably distorted (173.6 degrees); the enamine double bond is reactive toward unsaturated amides (providng 4) and methyl vinyl ketone (providing 10). (C) 1997 Elsevier Science Ltd.

引用

页码：3963 / 3966

页数：4

共 7 条

[1] CYCLOADDITIONS OF FLUOROALLENE AND 1,1-DIFLUOROALLENE [J].

DOLBIER, WR .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (03) :63-69

[2] CONVENIENT SYNTHESIS OF DENSELY FUNCTIONALIZED N-SUBSTITUTED 4-METHYLENE-2-OXAZOLIDINONE [J].

KIMURA, M ;

KURE, S ;

YOSHIDA, Z ;

TANAKA, S ;

FUGAMI, K ;

TAMARU, Y .

TETRAHEDRON LETTERS, 1990, 31 (34) :4887-4890

[3] ASYMMETRIC [2 + 2] CYCLOADDITION REACTION CATALYZED BY A CHIRAL TITANIUM REAGENT [J].

NARASAKA, K ;

HAYASHI, Y ;

SHIMADZU, H ;

NIIHATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) :8869-8885

[4] PALLADIUM-CATALYZED REACTION OF METHYLENEOXAZOLIDINONES - INTERVENTION OF A PALLADIUM COMPLEX OF A Y-SHAPED CH2C(NTS)CH2 MOLECULE AS AN ISOSTRUCTURE OF TRIMETHYLENEMETHANE [J].

OHE, K ;

ISHIHARA, T ;

CHATANI, N ;

MURAI, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9646-9647

[5] (PHENYLSULFONYL)ALLENES AS SUBSTRATES FOR CYCLOADDITION REACTIONS - INTRAMOLECULAR CYCLIZATIONS ONTO UNACTIVATED ALKENES [J].

PADWA, A ;

MESKE, M ;

MURPHREE, SS ;

WATTERSON, SH ;

NI, ZJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (27) :7071-7080

[6] CONVENIENT SYNTHESIS OF 4-METHYLENE-2-OXAZOLIDINONES AND 4-METHYLENETETRAHYDRO-1,3-OXAZIN-2-ONES VIA TRANSITION-METAL-CATALYZED INTRAMOLECULAR ADDITION OF NITROGEN ATOM TO ACETYLENIC TRIPLE BOND [J].

TAMARU, Y ;

KIMURA, M ;

TANAKA, S ;

KURE, S ;

YOSHIDA, Z .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (10) :2838-2849

[7]

TODA F, 1994, ANGEW CHEM INT EDIT, V33, P1757, DOI 10.1002/anie.199417571

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