Synthesis of 2-Aminoindolizines by 1,3-Dipolar Cycloaddition of Pyridinium Ylides with Electron-Deficient Ynamides

被引:124
作者
Brioche, Julien [1 ]
Meyer, Christophe [1 ]
Cossy, Janine [1 ]
机构
[1] PSL Res Univ, Lab Chim Organ, Inst Chem Biol & Innovat CBI, ESPCI ParisTech,CNRS UMR8231, F-75231 Paris 05, France
关键词
HIGHLY EFFICIENT SYNTHESIS; ONE-POT SYNTHESIS; FUNCTIONALIZED INDOLIZINES; CATALYZED CYCLIZATION; POLYSUBSTITUTED INDOLIZINES; CONVENIENT SYNTHESIS; C-C; ROUTE; HETEROCYCLES; NITROGEN;
D O I
10.1021/acs.orglett.5b01205
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Electron-deficient ynamides, possessing an ynoate or an ynone moiety, have been successfully involved for the first time in a 1,3-dipolar cycloaddition with stabilized pyridinium ylides. These reactions afford an efficient and general access toward a variety of substituted 2-aminoindolizines which can serve as useful precursors for the synthesis of other more complex nitrogen heterocycles.
引用
收藏
页码:2800 / 2803
页数:4
相关论文
共 68 条
[1]   A TDDFT Study of the Fluorescence Properties of Three Alkoxypyridylindolizine Derivatives [J].
Aittala, Pekka J. ;
Cramariuc, Oana ;
Hukka, Terttu I. ;
Vasilescu, Marilena ;
Bandula, Rodica ;
Lemmetyinen, Helge .
JOURNAL OF PHYSICAL CHEMISTRY A, 2010, 114 (26) :7094-7101
[2]   Nucleophilicity Parameters of Pyridinium Ylides and Their Use in Mechanistic Analyses [J].
Allgaeuer, Dominik S. ;
Mayer, Peter ;
Mayr, Herbert .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (40) :15216-15224
[3]   Pyridine Activation via Copper(I)-Catalyzed Annulation toward indolizines [J].
Barluenga, Jose ;
Lonzi, Giacomo ;
Riesgo, Lorena ;
Lopez, Luis A. ;
Tomas, Miguel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) :13200-13202
[4]  
Behnisch A., 1994, HOUBEN WEYL E, VE6b/1, P323
[5]   1,2-Disubstituted 4-Quinolones via Copper-Catalyzed Cyclization of 1-(2-Halophenyl)-2-en-3-amin-1-ones [J].
Bernini, Roberta ;
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Sferrazza, Alessio .
SYNTHESIS-STUTTGART, 2009, (07) :1209-1219
[6]   Synthesis of ynamides from formamides [J].
Brückner, D .
TETRAHEDRON, 2006, 62 (16) :3809-3814
[7]   Low temperature organocopper-mediated two-component cross coupling/cycloisomerization approach toward N-fused heterocycles [J].
Chernyak, Dmitri ;
Gadamsetty, Surendra Babu ;
Gevorgyan, Vladimir .
ORGANIC LETTERS, 2008, 10 (11) :2307-2310
[8]   Two-Component Approach Toward a Fully Substituted N-Fused Pyrrole Ring [J].
Chernyak, Dmitri ;
Skontos, Cathy ;
Gevorgyan, Vladimir .
ORGANIC LETTERS, 2010, 12 (14) :3242-3245
[9]   Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles [J].
Chuprakov, Stepan ;
Hwang, Frank W. ;
Gevorgyan, Vladimir .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) :4757-4759
[10]   Nef-Perkow Access to Indolizine Derivatives [J].
Coffinier, Didier ;
El Kaim, Laurent ;
Grimaud, Laurence .
SYNLETT, 2010, (16) :2474-2476