Reductive heterocyclizations via indium/iodine-promoted one-pot conversion of 2-nitroaryl aldehydes, ketones, and imines

被引:31
作者
Han, Rongbi
Son, Kee In
Ahn, Gil Hwan
Jun, Young Moo
Lee, Byung Min
Park, Younbong
Kim, Byeong Hyo [1 ]
机构
[1] Kwangwoon Univ, Dept Chem, Seoul 139701, South Korea
[2] Yanbian Univ, MOE, Key Lab Organism Funct Factors Changbai Mt, Jilin 133002, Peoples R China
[3] Korea Res Inst Chem Technol, Taejon 305600, South Korea
[4] Chungnam Natl Univ, Dept Chem, Taejon 305764, South Korea
基金
新加坡国家研究基金会;
关键词
indium and compounds; reduction; nitro compounds;
D O I
10.1016/j.tetlet.2006.08.027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Nitroaryl aldehydes, ketones, and imines were reductively cyclized to 2,1-benzisoxazoles with good yields in the presence of indium and iodine in MeOH. Under a similar condition, N-(2-nitrobenzylidene)anilines were produced mixtures of 2,1-benzisoxazoles and 3-anilino-2-phenyl-2H-indazoles. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7295 / 7299
页数:5
相关论文
共 39 条
[1]   Metal-mediated entry to functionalized 3-substituted 3-hydroxyindolin-2-ones via regiocontrolled carbonylallylation, bromoallylation, 1,3-butadien-2-ylation, propargylation, or allenylation reactions of isatins in aqueous media [J].
Alcaide, B ;
Almendros, P ;
Rodríguez-Acebes, R .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3198-3204
[2]   Photostimulated reductive cyclization of o-nitrophenylazo dyes using sodium hydroxide in isopropyl alcohol.: A new synthesis of 2-aryl-2H-benzotriazoles [J].
Baik, W ;
Yoo, CH ;
Koo, S ;
Kim, H ;
Hwang, YH ;
Kim, BH ;
Lee, SW .
HETEROCYCLES, 1999, 51 (08) :1779-1783
[3]   REDUCTIVE CYCLIZATION OF O-NITROPHENYLAZO DYES USING BAKERS-YEAST IN NAOH SOLUTION - A NEW SYNTHESIS OF 2-ARYL-2H-BENZOTRIAZOLES AND THEIR 1-OXIDES [J].
BAIK, W ;
PARK, TH ;
KIM, BH ;
JUN, YM .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5683-5685
[4]   Iodine-catalyzed synthesis of β-keto enol ethers [J].
Bhosale, RS ;
Bhosale, SV ;
Bhosale, SV ;
Wang, TY ;
Zubaidha, PK .
TETRAHEDRON LETTERS, 2004, 45 (39) :7187-7188
[5]   1993 RU-LEMIEUX-AWARD-LECTURE - ORGANOMETALLIC-TYPE REACTIONS IN AQUEOUS-MEDIA - A NEW CHALLENGE IN ORGANIC-SYNTHESIS [J].
CHAN, TH ;
LI, CJ ;
LEE, MC ;
WEI, ZY .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (05) :1181-1192
[6]   FACILE SYNTHESIS OF LOWER HALIDES OF INDIUM [J].
FREELAND, BH ;
TUCK, DG .
INORGANIC CHEMISTRY, 1976, 15 (02) :475-476
[7]   Indium and zinc mediated one-atom carbocycle enlargement in water [J].
Haberman, JX ;
Li, CJ .
TETRAHEDRON LETTERS, 1997, 38 (27) :4735-4736
[8]  
Han RB, 2006, HETEROCYCLES, V68, P1675
[9]   INDIUM-MEDIATED COUPLING OF ALDEHYDES WITH PROP-2-YNYL BROMIDES IN AQUEOUS-MEDIA [J].
ISAAC, MB ;
CHAN, TH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (10) :1003-1004
[10]   Studies on lactams .102. Environ-friendly approaches to densely functionalized beta-lactams [J].
Jayaraman, M ;
Manhas, MS ;
Bose, AK .
TETRAHEDRON LETTERS, 1997, 38 (05) :709-712