Low temperature organocopper-mediated two-component cross coupling/cycloisomerization approach toward N-fused heterocycles

被引：90

作者：

Chernyak, Dmitri ^{[1
]}

Gadamsetty, Surendra Babu ^{[1
]}

Gevorgyan, Vladimir ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 11期

关键词：

D O I：

10.1021/ol8008705

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Organocopper reagents smoothly react with heterocyclic propargyl mesylates at low temperature to produce Mused heterocycles. The copper reagent plays a "double duty" in this novel cascade transformation, which proceeds via an S(N)2' substitution followed by a subsequent cycloisomerization step.

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收藏

页码：2307 / 2310

页数：4

相关论文

共 46 条

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

Alonso, F ;

Beletskaya, IP ;

Yus, M .

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

[2]

[Anonymous], 1994, ORGANOMETALLICS SYNT

[3] Recent advances in organocopper chemistry [J].

Caprio, Vittorio .

LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (05) :339-349

[4] Reaction of α-(N-carbamoyl)alkylcuprates with enantioenriched propargyl electrophiles:: Synthesis of enantioenriched 3-pyrrolines [J].

Dieter, R. Karl ;

Chen, Ningyi ;

Gore, Vinayak K. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (23) :8755-8760

[5] Reaction of α-(N-carbamoyl)alkylcuprates with propargyl substrates:: Synthetic route to a-amino allenes and Δ3-pyrrolines [J].

Dieter, RK ;

Chen, NY ;

Yu, HY ;

Nice, LE ;

Gore, VK .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2109-2119

[6] Synthesis of 3-pyrrolines, annulated 3-pyrrolines, and pyrroles from α-Amino allenes [J].

Dieter, RK ;

Yu, H .

ORGANIC LETTERS, 2001, 3 (24) :3855-3858

[7] Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles [J].

Dudnik, Alexander S. ;

Sromek, Anna W. ;

Rubina, Marina ;

Kim, Joseph T. ;

Kel'in, Alexander V. ;

Gevorgyan, Vladimir .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (04) :1440-1452

[8]

Facompré M, 2003, CANCER RES, V63, P7392

[9] Catalytic carbophilic activation:: Catalysis by platinum and gold π acids [J].

Fuerstner, Alois ;

Davies, Paul W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) :3410-3449

[10] Pharmacokinetics and pharmacodynamics of TF-505, a novel nonsteroidal 5α-reductase inhibitor, in normal subjects treated with single or multiple doses [J].

Fujita, T ;

Matsumoto, Y ;

Kimura, T ;

Yokota, S ;

Sawada, M ;

Majima, M ;

Ohtani, Y ;

Kumagai, Y .

BRITISH JOURNAL OF CLINICAL PHARMACOLOGY, 2002, 54 (03) :283-294

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