Unexpected facile sequential halolactamization-hydroxylation of 2,3-allenamides with CuX2 for the efficient synthesis of 4-halo-5-hydroxypyrrol-2(5H)-ones

被引：62

作者：

Ma, SM ^{[1
]}

Xie, HX ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Organomet Chem Lab, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 24期

关键词：

D O I：

10.1021/ol006504j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 4-Halo-5-hydroxypyrrol-2(5H)-ones were synthesized from the efficient sequential halolactamization-hydroxylation reaction of 4-monosubstituted 2,3-allenamides with CuX2 (X = Br, CI) in high yields. Halolactamization of fully substituted 2,3-dienamide (1f) afforded 4-halo-pyrrol-2(5H)-ones.

引用

页码：3801 / 3803

页数：3

共 30 条

[1] A ONE-STEP CONVERSION OF N-ACYLAMINOKETONES INTO 5-ALKYLIDENE-3-PYRROLIN-2-ONES [J].

ANSELMI, C ;

CAMPARINI, A ;

SCOTTON, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (03) :687-689

[2] Cyanation of alpha-ketoalkynes catalyzed by nickel in water [J].

Arzoumanian, H ;

Jean, M ;

Nuel, D ;

Garcia, JL ;

Rosas, N .

ORGANOMETALLICS, 1997, 16 (12) :2726-2729

[3] PSEUDOESTERS AND DERIVATIVES .22. SYNTHESIS OF 5-HYDROXY-3-PYRROLIN-2-ONES AND 5-HYDROXYPYRROLIDIN-2-ONES BY AMMONOLYSIS OF 5-METHOXYFURAN-2 (5H)-ONES AND DERIVATIVES [J].

FARINA, F ;

MARTIN, MV ;

PAREDES, MC ;

ORTEGA, MC ;

TITO, A .

HETEROCYCLES, 1984, 22 (08) :1733-1739

[4] THE SYNTHESIS OF 5-YLIDENEPYRROL-2(5H)-ONES FROM MALEIMIDES AND FROM PYRROL-2-(5H)-ONES [J].

GILL, GB ;

JAMES, GD ;

OATES, KV ;

PATTENDEN, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (21) :2567-2579

[5]

Himbert G, 1997, LIEBIGS ANN-RECL, P435

[6]

HIMBERT G, 1992, Z NATURFORSCH B, V47, P1785

[7]

HIMBERT G, 1997, Z NATURFORSCH B, P435

[8]

Ma SM, 2000, EUR J ORG CHEM, V2000, P1939

[9]

Ma SM, 1999, CHINESE J CHEM, V17, P545

[10] Palladium(0)-catalyzed cyclization reaction of polymer-supported aryl iodides with 1,2-allenyl carboxylic acids. A facile solid-phase synthesis of butenolides [J].

Ma, SM ;

Duan, DH ;

Shi, ZJ .

ORGANIC LETTERS, 2000, 2 (10) :1419-1422

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