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
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 41期
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
[31]   Indium metal as a reducing agent in organic synthesis [J].
Pitts, MR ;
Harrison, JR ;
Moody, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (09) :955-977
[32]   Indium in organic synthesis [J].
Podlech, J ;
Maier, TC .
SYNTHESIS-STUTTGART, 2003, (05) :633-655
[33]   Indium as a reducing agent.: Chemoselective reduction of α-halocarbonyl compounds and benzyl halides by indium metal in water under sonication [J].
Ranu, BC ;
Dutta, P ;
Sarkar, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (09) :1139-1140
[34]   Stereoselective debromination of aryl-substituted vic-dibromide with indium metal [J].
Ranu, BC ;
Guchhait, SK ;
Sarkar, A .
CHEMICAL COMMUNICATIONS, 1998, (19) :2113-2114
[35]   A novel, simple, chemoselective and practical protocol for the reduction of azides using In/NH4Cl [J].
Reddy, GV ;
Rao, GV ;
Iyengar, DS .
TETRAHEDRON LETTERS, 1999, 40 (20) :3937-3938
[36]  
Yamamoto H., 2004, MAIN GROUP METALS OR, V1, P323
[37]   Indium-mediated radical cyclization of iodoalkenes and iodoalkynes with and without allylic and propargylic leaving groups [J].
Yanada, R ;
Obika, S ;
Nishimori, N ;
Yamauchi, M ;
Takemoto, Y .
TETRAHEDRON LETTERS, 2004, 45 (11) :2331-2334
[38]   Indium-mediated atom-transfer and reductive radical cyclizations of lodoalkynes: Synthesis and biological evaluation of HIV-protease inhibitors [J].
Yanada, R ;
Koh, Y ;
Nishimori, N ;
Matsumura, A ;
Obika, S ;
Mitsuya, H ;
Fujii, N ;
Takemoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2417-2422
[39]   Indium-mediated atom-transfer cyclizations and reductive cyclizations [J].
Yanada, R ;
Nishimori, N ;
Matsumura, A ;
Fujii, N ;
Takemoto, Y .
TETRAHEDRON LETTERS, 2002, 43 (26) :4585-4588
1234