Ceric ammonium nitrate (CAN): an efficient and eco-friendly catalyst for the one-pot synthesis of alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl)methanes at room temperature

被引:44
作者
Brahmachari, Goutam [1 ]
Banerjee, Bubun [1 ]
机构
[1] Visva Bharati Univ, Dept Chem, Lab Nat Prod & Organ Synth, Santini Ketan 731235, W Bengal, India
关键词
CYCLIC-NUCLEOTIDE PHOSPHODIESTERASE; MULTICOMPONENT REACTION; 4-COMPONENT SYNTHESIS; PYRIMIDINE-DERIVATIVES; RECYCLABLE CATALYST; RADICAL-ADDITION; INHIBITION; FACILE; ACID; SCAFFOLDS;
D O I
10.1039/c5ra04723d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple, facile and convenient practical method for the one-pot synthesis of biologically relevant alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl) methane scaffolds (3a-3u) has been developed using ceric ammonium nitrate (CAN) as a commercially available and eco-friendly catalyst via pseudo three-component condensation reaction between aldehydes and 6-aminouracils in aqueous ethanol at room temperature. The salient features of the present protocol are mild reaction conditions, good to excellent yields, high atom-economy, environmentally benignity, easy isolation of products, no column chromatographic separation and reusability of reaction media.
引用
收藏
页码:39263 / 39269
页数:7
相关论文
共 71 条
[1]   Novel pyrazolo[3,4-d]pyrimidine-based inhibitors of Staphlococcus aureus DNA polymerase III:: Design, synthesis, and biological evaluation [J].
Ali, A ;
Taylor, GE ;
Ellsworth, K ;
Harris, G ;
Painter, R ;
Silver, LL ;
Young, K .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (10) :1824-1830
[2]  
[Anonymous], 1984, Comprehensive Heterocyclic Chemistry
[3]   Reactions of 6-aminouracils: The first simple, fast, and highly efficient synthesis of bis(6-aminopyrimidonyl)methanes (BAPMs) using thermal or microwave-assisted solvent-free methods [J].
Azizian, Javad ;
Mohammadizadeh, Mohammad R. ;
Teimouri, Fatemeh ;
Mohammadi, Ali A. ;
Karimi, Ali R. .
SYNTHETIC COMMUNICATIONS, 2006, 36 (23) :3631-3638
[4]   Ammonium chloride catalysed one-pot multicomponent synthesis of 1,8-dioxo-octahydroxanthenes and N-aryl-1,8-dioxodecahydroacridines under solvent free conditions [J].
Banerjee, Bubun ;
Brahmachari, Goutam .
JOURNAL OF CHEMICAL RESEARCH, 2014, (12) :745-750
[5]   Formation of Aryl-bis (6-Amino-1,3-Dimethyluracil-5-yl) Methanes by reaction of 6-Amino-1, 3-Dimethyluracil with Aromatic Aldehydes [J].
Bansal, Ranju ;
Kumar, R. Sunil ;
Kumar, Gulshan ;
Thota, Sridhar ;
Thamotharan, S. ;
Parthasarathi, V. ;
Linden, Anthony .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (06) :1789-1795
[6]   New pyrrolo[2,1-f]purine-2,4-dione and imidazo[2,1-f]purine-2,4-dione derivatives as potent and selective human A3 adenosine receptor antagonists [J].
Baraldi, PG ;
Preti, D ;
Tabrizi, MA ;
Fruttarolo, F ;
Romagnoli, R ;
Zaid, NA ;
Moorman, AR ;
Merighi, S ;
Varani, K ;
Borea, PA .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (14) :4697-4701
[7]  
Barnette M S, 1999, Prog Drug Res, V53, P193
[8]   NEW SYNTHESIS OF URIC ACID AND 1,7-DIMETHYLURIC ACID [J].
BILLS, CW ;
SWEETING, OJ ;
GEBURA, SE ;
MEEK, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (12) :4633-&
[9]   5-SUBSTITUTED PYRIMIDINE NUCLEOSIDES AND NUCLEOTIDES [J].
BRADSHAW, TK ;
HUTCHINSON, DW .
CHEMICAL SOCIETY REVIEWS, 1977, 6 (01) :43-62
[10]   Eco-friendly, One-Pot Multicomponent Synthesis of Pyran Annulated Heterocyclic Scaffolds at Room Temperature Using Ammonium or Sodium Formate as Non-toxic Catalyst [J].
Brahmachari, G. ;
Laskar, S. ;
Banerjee, B. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 :E303-E308