Copper-Catalyzed Annulation of 2-Formylazoles with o-Aminoiodoarenes

被引:70
作者
Reeves, Jonathan T. [1 ]
Fandrick, Daniel R. [1 ]
Tan, Zhulin [1 ]
Song, Jinhua J. [1 ]
Lee, Heewon [1 ]
Yee, Nathan K. [1 ]
Senanayake, Chris H. [1 ]
机构
[1] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, Ridgefield, CT 06877 USA
关键词
BIOLOGICAL EVALUATION; N-ARYLATION; DERIVATIVES;
D O I
10.1021/jo9025644
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of catalytic CuI and sparteine, 2-formyl-pyrroles can be annulated with o-aminoiodoarenes to give Substituted pyrrolo[1,2-a]quinoxalines and related heterocycles. The reaction also works for annulation of 2-formylindoles, 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazole.
引用
收藏
页码:992 / 994
页数:3
相关论文
共 18 条
[1]   Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles [J].
Antilla, JC ;
Baskin, JM ;
Barder, TE ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5578-5587
[2]  
CHEESEMAN GW, 1965, CHEM IND-LONDON, P1382
[3]   IODIDE DEALKYLATION OF BENZYL, PMB, PNB, AND T-BUTYL N-ACYL AMINO-ACID ESTERS VIA LITHIUM ION COORDINATION [J].
FISHER, JW ;
TRINKLE, KL .
TETRAHEDRON LETTERS, 1994, 35 (16) :2505-2508
[4]   Synthesis and preliminary in vitro evaluation of antimycobacterial activity of new pyrrolo[1,2-a]quinoxaline-carboxylic acid hydrazide derivatives [J].
Guillon, J ;
Reynolds, RC ;
Leger, JM ;
Guie, MA ;
Massip, S ;
Dallemagne, P ;
Jarry, C .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2004, 19 (06) :489-495
[5]  
Guillon J., 1998, Pharmacy and Pharmacology Communications, V4, P33
[6]   Synthesis of new pyrrolo[1,2-a]quinoxalines:: potential non-peptide glucagon receptor antagonists [J].
Guillon, J ;
Dallemagne, P ;
Pfeiffer, B ;
Renard, P ;
Manechez, D ;
Kervran, A ;
Rault, S .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1998, 33 (04) :293-308
[7]   Synthesis of new 2-(aminomethyl)-4-phenylpyrrolo[1,2-a]quinoxalines and their preliminary in-vivo central dopamine antagonist activity evaluation in mice [J].
Guillon, J ;
Boulouard, M ;
Lisowski, V ;
Stiebing, S ;
Lelong, V ;
Dallemagne, P ;
Rault, S .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 2000, 52 (11) :1369-1375
[8]   Synthesis, analytical behaviour and biological evaluation of new 4-substituted pyrrolo[1,2-a]quinoxalines as antileishmanial agents [J].
Guillon, Jean ;
Forfar, Isabelle ;
Mamani-Matsuda, Maria ;
Desplat, Vanessa ;
Saliege, Marion ;
Thiolat, Denis ;
Massip, Stephane ;
Tabourier, Anais ;
Leger, Jean-Michel ;
Dufaure, Benoit ;
Haumont, Gilbert ;
Jarry, Christian ;
Mossalayi, Djavad .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (01) :194-210
[9]   Two alternatives for the synthesis of pyrrolo[1,2-a] quinoxaline derivatives [J].
Harrak, Y. ;
Weber, S. ;
Gomez, A. B. ;
Rosell, G. ;
Pujol, M. D. .
ARKIVOC, 2007, :251-259
[10]   Synthesis of substituted indolo[1,2-a]quinoxalines [J].
Joseph, MS ;
Basanagoudar, LD .
SYNTHETIC COMMUNICATIONS, 2003, 33 (05) :851-862