A Clean, Highly Efficient and One-Pot Green Synthesis of Aryl/Alkyl/Heteroaryl-Substituted Bis(6-amino-1,3-dimethyluracil-5-yl)methanes in Water

被引:44
作者
Das, Subrata [1 ]
Thakur, Ashim Jyoti [1 ]
机构
[1] Tezpur Univ, Dept Chem Sci, Tezpur 784028, Assam, India
关键词
Nitrogen heterocycles; Green chemistry; Heterocycles; Water chemistry; CROSS-METATHESIS REACTIONS; C-H ACTIVATION; ROOM-TEMPERATURE; ORGANIC-REACTIONS; ADENOSINE A(1); URACIL; DERIVATIVES; CHEMISTRY; CATALYST; DNA;
D O I
10.1002/ejoc.201001581
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient green synthesis of aryl/alkyl/heteroaryl-substituted bis(6-amino-1,3-dimethyluracil-5-yl)methanes by the condensation of 6-amino-1,3-dimethyluracil with aldehydes (aromatic, aliphatic and heterocyclic) in water at room temperature is described. No dehydrating agent, heat, catalyst, surfactant or additive was used. The structures of the compounds were established by spectroscopic methods and single-crystal X-ray crystallography.
引用
收藏
页码:2301 / 2308
页数:8
相关论文
共 105 条
[1]   Efficient Asymmetric α-Oxyamination of Aldehydes by Resin-Supported Peptide Catalyst in Aqueous Media [J].
Akagawa, Kengo ;
Fujiwara, Takuma ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
ORGANIC LETTERS, 2010, 12 (08) :1804-1807
[2]   Roles of water for chemical reactions in high-temperature water [J].
Akiya, N ;
Savage, PE .
CHEMICAL REVIEWS, 2002, 102 (08) :2725-2750
[3]   LUMINESCENCE PROBES - THE EU-3+-CRYPTATES AND TB-3+-CRYPTATES OF POLYPYRIDINE MACROBICYCLIC LIGANDS [J].
ALPHA, B ;
BALZANI, V ;
LEHN, JM ;
PERATHONER, S ;
SABBATINI, N .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (12) :1266-1267
[4]  
Alpha B., 1987, ANGEW CHEM, V99, P1310, DOI DOI 10.1002/ANGE.19870991226
[5]  
Anastas P., 1998, GREEN CHEM THEORY PR
[6]  
[Anonymous], 2002, CLEAN SOLVENTS ALTER, DOI DOI 10.1021/BK-2002-0819
[7]   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
[8]   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
[9]   Synthesis of a series of 8-(substituted-phenyl)xanthines and a study on the effects of substitution pattern of phenyl substituents on affinity for adenosine A1 and A2A receptors [J].
Bansal, Ranju ;
Kumar, Gulshan ;
Gandhi, Deepika ;
Young, Louise C. ;
Harvey, Alan L. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (05) :2122-2127
[10]   Clean synthesis in water: uncatalysed preparation of ylidenemalononitriles [J].
Bigi, F ;
Conforti, ML ;
Maggi, R ;
Piccinno, A ;
Sartori, G .
GREEN CHEMISTRY, 2000, 2 (03) :101-103