Thermal and acid-catalyzed Hofmann-Martius rearrangement of 3-N-aryl-2-oxindoles into 3-(arylamino)-2-oxindoles

被引：59

作者：

Magnus, Philip ^{[1
]}

Turnbull, Rachel ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 16期

关键词：

D O I：

10.1021/ol061191z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Hofmann-Martius rearrangement of 3-N-aryl-2-oxindoles into 3-(arylamino)-2-oxindoles under thermal and acid-catalyzed conditions is described.

引用

页码：3497 / 3499

页数：3

共 20 条

[1]

AKIRA I, 1982, HETEROCYCLES, V19, P2139

[2]

ALDER W, 1971, MECH ORGANIC CHEM, P78

[3] Proton-catalyzed hydroamination and hydroarylation reactions of anilines and alkenes: A dramatic effect of counteranions on reaction efficiency [J].

Anderson, LL ;

Arnold, J ;

Bergman, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (42) :14542-14543

[4]

Banthorpe D. V., 1968, CHEM AMINO GROUP, P585

[5]

Bruce J.M., 1957, J CHEM SOC, V4789, DOI 10.1039/jr9570004789

[6] Indol-2-one intermediates:: Mechanistic evidence and synthetic utility.: Total syntheses of (±)-flustramines A and C [J].

Fuchs, JR ;

Funk, RL .

ORGANIC LETTERS, 2005, 7 (04) :677-680

[7] A mild thermal and acid-catalyzed rearrangement of O-aryl ethers into ortho-hydroxy arenes [J].

Goldberg, FW ;

Magnus, P ;

Turnbull, R .

ORGANIC LETTERS, 2005, 7 (20) :4531-4534

[8] MECHANISM OF REARRANGEMENT OF N-ALKYLANILINES [J].

HART, H ;

KOSAK, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (01) :116-&

[9] Synthesis and structure-activity relationships of 3-aryloxindoles: A new class of calcium-dependent, large conductance potassium (maxi-K) channel openers with neuroprotective properties [J].

Hewawasam, P ;

Erway, M ;

Moon, SL ;

Knipe, J ;

Weiner, H ;

Boissard, CG ;

Post-Munson, DJ ;

Gao, Q ;

Huang, S ;

Gribkoff, VK ;

Meanwell, NA .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (07) :1487-1499

[10]

Hofmann A. W., 1871, Ber. Dtsch. Chem. Ges., V4, P742

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