One-pot synthesis of 2-(2-hydroxyaryl)quinolines:: reductive coupling reactions of 2′-hydroxy-2-nitrochalcones

被引:24
作者
Barros, AIRNA
Silva, AMS [1 ]
机构
[1] Univ Aveiro, Dept Chem, P-3810193 Aveiro, Portugal
[2] Univ Tras Montes & Alto Douro, Dept Chem, P-5001911 Vila Real, Portugal
关键词
2-(2-hydroxyaryl)quinolines; 2-(2-hydroxyaryl)quinolines-N-oxides; 2 '-hydroxy-2-nitrochalcones; reduction; cyclodehydration;
D O I
10.1016/S0040-4039(03)01374-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot synthesis of novel 2-(2-hydroxyaryl)quinolines have been developed from the intramolecular reductive coupling reactions of 2'-hydroxy-2-nitrochalcones, induced by stannous chloride in acidic medium (HCl/AcOH). In some cases these transformations can be performed with ammonium formate/Pd-C in methanol. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5893 / 5896
页数:4
相关论文
共 24 条
[1]   The Vilsmeier cyclization of 2′-azido and 2′-aminochalcones -: a mild one pot synthesis of 2-aryl-4-chloroquinoline and its N-formyl-1,2-dihydro derivatives [J].
Akila, S ;
Selvi, S ;
Balasubramanian, K .
TETRAHEDRON, 2001, 57 (16) :3465-3469
[2]  
Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109
[3]   Applications of Baylis-Hillman chemistry:: one-pot convenient synthesis of functionalized (1H)-quinol-2-ones and quinolines [J].
Basavaiah, D ;
Reddy, RM ;
Kumaragurubaran, N ;
Sharada, DS .
TETRAHEDRON, 2002, 58 (19) :3693-3697
[4]   Preparation of quinolines by reduction of ortho-nitroarenes with zinc in near-critical water [J].
Boix, C ;
de la Fuente, JM ;
Poliakoff, M .
NEW JOURNAL OF CHEMISTRY, 1999, 23 (06) :641-643
[5]   Intramolecular amination catalysed by ruthenium and palladium. Synthesis of 2-acyl indoles and 2-aryl quinolines by carbonylation of 2-nitrochalcones [J].
Cenini, S ;
Bettettini, E ;
Fedele, M ;
Tollari, S .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 111 (1-2) :37-41
[6]   THE CHEMISTRY OF 2'-AMINO ANALOGS OF 2'-HYDROXYCHALCONE AND ITS DERIVATIVES [J].
DONNELLY, JA ;
FARRELL, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1757-1761
[7]  
HIRAK U, 1989, Patent No. 287951
[8]  
Jones G., 1996, Elsevier, V5, P167
[9]   A convenient and highly regioselective one-pot synthesis of quinolines by addition of a Vilsmeier-type reagent to N-arylimines [J].
Katritzky, AR ;
Arend, M .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9989-9991
[10]   Some aspects of reduced quinoline chemistry [J].
Kouznetsov, V ;
Palma, A ;
Ewert, C ;
Varlamov, A .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (04) :761-785