A synthesis of 5-hetaryl-3-(2-hydroxybenzoyl)pyrroles

被引:32
作者
Plaskon, Andrey S. [1 ,2 ]
Ryabukhin, Sergey V. [1 ,2 ]
Volochnyuk, Dmitriy M. [1 ,3 ]
Shivanyuk, Alexander N. [1 ,2 ]
Tolmachev, Andrey A. [2 ]
机构
[1] Enamine Ltd, UA-01103 Kiev, Ukraine
[2] Natl Taras Shevchenko Univ, UA-01033 Kiev, Ukraine
[3] Natl Acad Sci Ukraine, Inst Organ Chem, UA-02094 Kiev, Ukraine
关键词
3-formylchromone; pyrroles; hetarylmethylamines; recyclization; chlorotrimethylsilane;
D O I
10.1016/j.tet.2008.04.041
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and versatile procedure for the synthesis of 5-hetaryl-3-(2-hydroxybenzoyl)-1H-pyrroles and 4-(2-hydroxybenzoyl)-1H-pyrrole-2-carboxylic acid derivatives was established on the basis of TMSCl promoted recyclization of 3-formylchromone with various hetarylmethylamines and glycine derivatives. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5933 / 5943
页数:11
相关论文
共 55 条
[1]  
Allimony HA, 1996, INDIAN J CHEM B, V35, P1026
[2]  
Bean G.P., 1990, PYRROLES, V48, P105
[3]   Synthesis of 1-aminoimidazolidin-4-one and 1-aminoimidazolidin-2-one based compounds: an interesting divergence in methodology [J].
Blass, Benjamin E. ;
Coburn, Keith ;
Fairweather, Neil ;
Fluxe, Andrew ;
Hodson, Steve ;
Jackson, Chris ;
Janusz, John ;
Lee, Wenlin ;
Ridgeway, Jim ;
White, Ron ;
Wu, Shengde .
TETRAHEDRON LETTERS, 2006, 47 (42) :7497-7499
[4]   NONPEPTIDE ANGIOTENSIN-II ANTAGONISTS - N-PHENYL-1H-PYRROLE DERIVATIVES ARE ANGIOTENSIN-II RECEPTOR ANTAGONISTS [J].
BOVY, PR ;
REITZ, DB ;
COLLINS, JT ;
CHAMBERLAIN, TS ;
OLINS, GM ;
CORPUS, VM ;
MCMAHON, EG ;
PALOMO, MA ;
KOEPKE, JP ;
SMITS, GJ ;
MCGRAW, DE ;
GAW, JF .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (01) :101-110
[5]   DNA binding ligands targeting drug-resistant Gram-positive bacteria.: Part 2:: C-terminal benzimidazoles and derivatives [J].
Bürli, RW ;
Jones, P ;
McMinn, D ;
Le, Q ;
Duan, JX ;
Kaizerman, JA ;
Difuntorum, S ;
Moser, HE .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (05) :1259-1263
[6]   DNA binding ligands targeting drug-resistant gram-positive bacteria.: Part 1:: Internal benzimidazole derivatives [J].
Bürli, RW ;
McMinn, D ;
Kaizerman, JA ;
Hu, WH ;
Ge, YG ;
Pack, Q ;
Jiang, V ;
Gross, M ;
Garcia, M ;
Tanaka, R ;
Moser, HE .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (05) :1253-1257
[7]  
BUTERA JA, 1992, Patent No. 5084463
[8]   REACTION OF SOME DIKETONES WITH 5-AMINOLEVULINIC ACID IN ACID-SOLUTION [J].
BUTLER, AR ;
GEORGE, SD .
TETRAHEDRON, 1993, 49 (32) :7017-7026
[9]   Estrogen receptor β selective ligands:: Discovery and SAR of novel heterocyclic ligands [J].
Chesworth, R ;
Wessel, MD ;
Heyden, L ;
Mangano, FM ;
Zawistoski, M ;
Gegnas, L ;
Galluzzo, D ;
Lefker, B ;
Cameron, KO ;
Tickner, J ;
Lu, BH ;
Castleberry, TA ;
Petersen, DN ;
Brault, A ;
Perry, P ;
Ng, O ;
Owen, TA ;
Pan, L ;
Ke, HZ ;
Brown, TA ;
Thompson, DD ;
DaSilva-Jardine, P .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (24) :5562-5566
[10]   REACTIONS OF FORMYLCHROMONE DERIVATIVES .5. TRANSFORMATIONS OF 3-FORMYLCHROMONES INTO PYRROLES AND PYRIDINES [J].
CLARKE, PD ;
FITTON, AO ;
KOSMIRAK, M ;
SUSCHITZKY, H ;
SUSCHITZKY, JL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (08) :1747-1756