Silver-Catalyzed Intramolecular Cyclization of o-(1-Alkynyl)benzamides: Efficient Synthesis of (1H)-Isochromen-1-imines

被引：61

作者：

Liu, Guannan ^{[1
]}

Zhou, Yu ^{[1
]}

Ye, Deju ^{[1
]}

Zhang, Dengyou ^{[1
]}

Ding, Xiao ^{[1
]}

Jiang, Hualiang ^{[1
,2
]}

Liu, Hong ^{[1
]}

机构：

[1] Chinese Acad Sci, Drug Discovery & Design Ctr, State Key Lab Drug Res, Shanghai Inst Mat Med,Shanghai Inst Biol Sci, Shanghai 201203, Peoples R China

[2] E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 16期

基金：

中国国家自然科学基金;

关键词：

intramolecular cyclization; (1H)-isochromen-1-imines; organic catalysis; regioselectivity; silver catalyst; synthetic methods; MULTIPLE-MYELOMA; ALKYNES; ISOQUINOLINES; HYDROAMINATION; ISOCOUMARINS; DERIVATIVES; ROUTE; BONDS; ACIDS;

D O I：

10.1002/adsc.200900381

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient avenue for the facile and atom-economic synthesis of (1H)-isochromen-1-imines has been developed, and a broad spectrum of substrates can participate in the process effectively to produce the desired products in good yields. Significantly, this is the first report of the synthesis of (1H)-isochromen-1-imines that involves a silver(I)-catalyzed, regiocontrolled intramolecular addition of the carbonyl group of the amide moiety towards an alkyne.

引用

页码：2605 / 2610

页数：6

共 37 条

[1] A novel pyrrole synthesis [J].

Agarwal, S ;

Knölker, HJ .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (21) :3060-3062

[2] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[3] Practical synthesis and elaboration of methyl 7-chloroindole-4-carboxylate [J].

Alper, PB ;

Nguyen, KT .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :2051-2053

[4] Silver-mediated synthesis of heterocycles [J].

Alvarez-Corral, Miriam ;

Munoz-Dorado, Manuel ;

Rodirguez-Garcia, Ignacio .

CHEMICAL REVIEWS, 2008, 108 (08) :3174-3198

[5]

[Anonymous], 2005, ANGEW CHEM

[6] Direct Mannich and nitro-Mannich reactions with non-activated imines:: AgOTf-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines [J].

Asao, N ;

Yudha, S ;

Nogami, T ;

Yamamoto, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5526-5528

[7] A remarkable accelerating effect of Ag-salt on intramolecular cyclization of o-(1-alkynyl)benzenesulfonamides [J].

Barange, Deepak Kumar ;

Nishad, T. C. ;

Swamy, N. Kumara ;

Bandameedi, Venkanna ;

Kumar, Dinesh ;

Sreekanth, Bukkapattanam R. ;

Vyas, K. ;

Pal, Manojit .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8547-8550

[8] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].

Beller, M ;

Seayad, J ;

Tillack, A ;

Jiao, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398

[9]

Beller M, 2004, ANGEW CHEM, V116, P3448

[10]

BONATE P, 2003, P AM SOC CLIN ONCOL

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