Tungstic acid-catalyzed synthesis of 3,3-bis(1H-indol-3-yl)indolin-2-one derivatives

被引:10
作者
Patel, Gautam M. [1 ]
Deota, Pradeep T. [1 ]
机构
[1] Maharaja Sayajirao Univ Baroda, Dept Appl Chem, Fac Engn & Technol, Vadodara 390001, India
关键词
indole; isatin; oxindole; tungstic acid; HYDROGEN-PEROXIDE; EFFICIENT; INDOLE; OXINDOLE; ALKALOIDS; ALDEHYDES; ISATIN;
D O I
10.1515/hc-2013-0142
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tungstic acid was used as a low-cost and readily available heterogeneous catalyst for the synthesis of 3,3-bis(1H-indol-3-yl)indolin-2-one derivatives from indoles. The reaction parameters, including catalyst quantity, solvents, temperature, and time were optimized. The present method has several advantages, such as mild conditions, simple work-up, elimination of anhydrous condition, easy recovery of catalyst and its recyclability as compared with existing methods.
引用
收藏
页码:421 / 424
页数:4
相关论文
共 37 条
[1]   Silica sulfuric acid a novel and heterogeneous catalyst for the synthesis of some new oxindole derivatives [J].
Azizian, Javad ;
Mohammadi, Ali A. ;
Karimi, Narges ;
Mohammadizadeh, Mohammad R. ;
Karimi, Ali R. .
CATALYSIS COMMUNICATIONS, 2006, 7 (10) :752-755
[2]   A convenient method of synthesis of bis-indolylmethanes:: Indium trichloride catalyzed reactions of indole with aldehydes and Schiff's bases. [J].
Babu, G ;
Sridhar, N ;
Perumal, PT .
SYNTHETIC COMMUNICATIONS, 2000, 30 (09) :1609-1614
[3]   Synthesis and evaluation of anti-HIV activity of isatin β-thiosemicarbazone derivatives [J].
Bal, TR ;
Anand, B ;
Yogeeswari, P ;
Sriram, D .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (20) :4451-4455
[4]   Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions [J].
Bandgar, BP ;
Shaikh, KA .
TETRAHEDRON LETTERS, 2003, 44 (09) :1959-1961
[5]   LEWIS-ACID-INDUCED ELECTROPHILIC SUBSTITUTION IN INDOLES WITH ACETONE .2. [J].
CHATTERJEE, A ;
MANNA, S ;
BANERJI, J ;
PASCARD, C ;
PRANGE, T ;
SHOOLERY, JN .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (02) :553-555
[6]   Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones [J].
Chen, DP ;
Yu, LB ;
Wang, PG .
TETRAHEDRON LETTERS, 1996, 37 (26) :4467-4470
[7]   New green catalytic manufacture of glutaric acid from the oxidation of cyclopentane-1,2-diol with aqueous hydrogen peroxide [J].
Chen, Hui ;
Dai, Wei-Lin ;
Gao, Ruihua ;
Cao, Yong ;
Li, Hexing ;
Fan, Kangnian .
APPLIED CATALYSIS A-GENERAL, 2007, 328 (02) :226-236
[8]   Microwave supported synthesis of some novel 1,3-Diarylpyrazino[1,2-a] benzimidazole derivatives and investigation of their anticancer activities [J].
Demirayak, Seref ;
Kayagil, Ismail ;
Yurttas, Leyla .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (01) :411-416
[9]   Reaction of tungstic acid hydrogen peroxide with endo-dicyclopentadiene:: An unusual observation [J].
Deota, PT ;
Desai, R ;
Valodkar, V .
JOURNAL OF CHEMICAL RESEARCH-S, 1998, (09) :562-563
[10]   Synthesis of Oxindoles by Tandem Heck-Reduction-Cyclization (HRC) from a Single Bifunctional, in Situ Generated Pd/C Catalyst [J].
Felpin, Francois-Xavier ;
Ibarguren, Oier ;
Nassar-Hardy, Luma ;
Fouquet, Eric .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :1349-1352