AuBr3-catalyzed cyclization of o-(alkynyl)nitrobenzenes.: Efficient synthesis of isatogens and anthranils

被引：93

作者：

Asao, N ^{[1
]}

Sato, K ^{[1
]}

Yamamoto, Y ^{[1
]}

机构：

[1] Tohoku Univ, Dept Chem, Grad Sch Sci, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(03)01357-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclization of o-(arylalkynyl)nitrobenzenes was catalyzed by AuBr3 to produce the corresponding isatogens in good to high yields together with small amounts of anthranils. On the other hand, anthranils were obtained selectively when the AuBr3-catalyzed reaction was carried out using o-(alkylalkynyl)nitrobenzenes. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：5675 / 5677

页数：3

相关论文

共 14 条

[1] AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].

Asao, N ;

Takahashi, K ;

Lee, S ;

Kasahara, T ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651

[2]

Baek EK, 1996, B KOR CHEM SOC, V17, P993

[3] REACTIONS OF 1,2-DINITROPHENYLETHANOLS - INTRAMOLECULAR PARTICIPATION BY NITRO-GROUP [J].

BAKKE, JM .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, 29 (10) :1063-1066

[4]

Génisson VB, 2001, SYNLETT, P700

[5]

Hagen H., 1982, Chem. Abstr, V97, Patent No. 54147

[6]

HELMUT H, 1982, Patent No. 3047388

[7] PREPARATION AND ANTIBACTERIAL ACTIVITY OF ISATOGENS AND RELATED COMPOUNDS [J].

HOOPER, M ;

PATTERSO.DA ;

WIBBERLE.DG .

JOURNAL OF PHARMACY AND PHARMACOLOGY, 1965, 17 (11) :734-&

[8] Role of spin trapping and P2Y receptor antagonism in the neuroprotective effects of 2,2′-pyridylisatogen tosylate and related compounds [J].

Menton, K ;

Spedding, M ;

Gressens, P ;

Villa, P ;

Williamson, T ;

Markham, A .

EUROPEAN JOURNAL OF PHARMACOLOGY, 2002, 444 (1-2) :53-60

[9] SYNTHETIC METHODS INVOLVING NEIGHBORING GROUP INTERACTION IN ORTHO-SUBSTITUTED NITROBENZENE DERIVATIVES [J].

PRESTON, PN ;

TENNANT, G .

CHEMICAL REVIEWS, 1972, 72 (06) :627-+

[10] A one-step synthesis of 2-(2-pyridyl)-3H-indol-3-one N-oxide:: Is it an efficient spin trap for hydroxyl radical? [J].

Rosen, GM ;

Tsai, P ;

Barth, ED ;

Dorey, G ;

Casara, P ;

Spedding, M ;

Halpern, HJ .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4460-4463