Efficient One-Pot Synthesis of Acridinediones by Indium(III) Triflate-Catalyzed Reactions of β-Enaminones, Aldehydes, and Cyclic 1,3-Dicarbonyls

被引:36
作者
Quang Huy To [1 ]
Lee, Yong Rok [1 ]
Kim, Sung Hong [2 ]
机构
[1] Yeungnam Univ, Sch Chem Engn, Gyongsan 712749, South Korea
[2] Korea Basic Sci Inst, Anal Res Div, Daegu Ctr, Taegu 702701, South Korea
关键词
Acridinedione; Indium(III) triflate; beta-Enaminone; IONIC LIQUID-MEDIUM; MICROWAVE IRRADIATION; AQUEOUS-MEDIA; DERIVATIVES; 1,8-DIOXO-DECAHYDROACRIDINES; IN(OTF)(3); MILD; ACID;
D O I
10.5012/bkcs.2012.33.4.1170
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient one-pot synthesis of acridinediones by In(OTf)(3)-catalyzed reactions was developed starting from beta-enaminones, aldehydes, and cyclic 1,3-diketones. The key strategies of these reactions involve domino Knoevenagel condensation/Michael addition/cyclodehydration reaction.
引用
收藏
页码:1170 / 1176
页数:7
相关论文
共 33 条
[1]   Indium triflate - An efficient catalyst for hetero Diels-Alder reactions [J].
Ali, T ;
Chauhan, KK ;
Frost, CG .
TETRAHEDRON LETTERS, 1999, 40 (30) :5621-5624
[2]   One-pot Synthesis of 1,8-Dioxo-decahydroacridine Derivatives in Aqueous Media [J].
Balalaie, Saeed ;
Chadegani, Fatemeh ;
Darviche, Fatemeh ;
Bijanzadeh, Hamid Reza .
CHINESE JOURNAL OF CHEMISTRY, 2009, 27 (10) :1953-1956
[3]   Efficient aromatic and heteroatom acylations using catalytic indium complexes with lithium perchlorate [J].
Chapman, CJ ;
Frost, CG ;
Hartley, JP ;
Whittle, AJ .
TETRAHEDRON LETTERS, 2001, 42 (05) :773-775
[4]   Amberlyst-15: An efficient reusable heterogeneous catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines [J].
Das, B ;
Thirupathi, P ;
Mahender, I ;
Reddy, VS ;
Rao, YK .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 247 (1-2) :233-239
[5]   Structure-activity relationships for substituted bis(acridine-4-carboxamides): A new class of anticancer agents [J].
Gamage, SA ;
Spicer, JA ;
Atwell, GJ ;
Finlay, GJ ;
Baguley, BC ;
Denny, WA .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (13) :2383-2393
[6]   Advances in indium triflate catalyzed organic syntheses [J].
Ghosh, Rina ;
Maiti, Swarupananda .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 264 (1-2) :1-8
[7]  
Hua GP, 2005, CHINESE J ORG CHEM, V25, P1294
[8]   One-pot clean synthesis of 1,8-dioxo-decahydroacridines catalyzed by p-dodecylbenezenesulfonic acid in aqueous media [J].
Jin, TS ;
Zhang, JS ;
Guo, TT ;
Wang, AQ ;
Li, TS .
SYNTHESIS-STUTTGART, 2004, (12) :2001-2005
[9]  
Jung DH, 2009, B KOREAN CHEM SOC, V30, P1989
[10]   Synthesis and antimicrobial activities of novel bisacridine-1,8-dione derivatives [J].
Kaya, Muharrem ;
Yildirir, Yilmaz ;
Celik, Gokcen Y. .
MEDICINAL CHEMISTRY RESEARCH, 2011, 20 (03) :293-299