DABCO-based ionic liquids: introduction of two metal-free catalysts for one-pot synthesis of 1,2,4-triazolo[4,3-a]pyrimidines and pyrido[2,3-d]pyrimidines

被引:52
作者
Jamasbi, N. [1 ]
Irankhah-Khanghah, M. [1 ]
Shirini, F. [1 ]
Tajik, H. [1 ]
Langarudi, M. S. N. [1 ]
机构
[1] Univ Guilan, Coll Sci, Dept Chem, Rasht 4133519141, Iran
关键词
MICHAEL ADDITION; RECYCLABLE CATALYSTS; EFFICIENT SYNTHESIS; REUSABLE CATALYST; DERIVATIVES; GREEN; SYSTEM; ACID;
D O I
10.1039/c8nj01455h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Straightforward methods for the synthesis of 1,2,4-triazolo[4,3-a]pyrimidine and pyrido[2,3-d]pyrimidine derivatives are described through three-component condensation of aromatic aldehydes, malononitrile, and 3-amino-1,2,4-triazole or 6-amino-1,3-dimethyluracil. In both procedures two affordable and metal-free DABCO-based ionic liquids are employed as catalysts and the obtained outcomes are compared with each other. All reactions are performed under mild conditions during acceptable reaction times in good to high yields. After ensuring the efficiency of the catalysts in both reactions, four new derivatives are synthesized and their structures are characterized by FT-IR, H-1 NMR and C-13 NMR. Simplicity, easy work-up procedures and recoverability of the catalysts are other advantages of these methods.
引用
收藏
页码:9016 / 9027
页数:12
相关论文
共 64 条
[1]  
Abdolmohammadi S., 2012, INT J ORG CHEM, V2, P7, DOI [DOI 10.4236/IJ0C.2012.21002, DOI 10.4236/IJOC.2012.21002]
[2]   An Efficient Three Component One-Pot Synthesis of 5-Amino-7-aryl-7,8-dihydro-[1,2,4] triazolo[4,3-a]-pyrimidine-6-carbonitriles [J].
Ablajan, Keyume ;
Kamil, Wetengul ;
Tuoheti, Anagu ;
Wan-Fu, Sun .
MOLECULES, 2012, 17 (02) :1860-1869
[3]  
ALLURI H, 2015, B PHARMA CHEMICA, V7, P515
[4]   Facile synthesis of pyridopyrimidine and coumarin fused pyridine libraries over a Lewis base-surfactant-combined catalyst TEOA in aqueous medium [J].
Bhattacharyya, Pranabes ;
Paul, Sanjay ;
Das, Asish R. .
RSC ADVANCES, 2013, 3 (10) :3203-3208
[5]   STUDIES ON URACILS .10. A FACILE ONE-POT SYNTHESIS OF PYRIDO[2,3-D]PYRIMIDINES AND PYRAZOLO[3,4-D]PYRIMIDINES [J].
BHUYAN, P ;
BORUAH, RC ;
SANDHU, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :568-571
[6]   Synthesis and Biological Activity of ω-(5-aryl-1,3,4-oxadiazol-2-thio)- and ω-(5-aryl-l,3,4-oxadiazol-2-thioacetoxyl)-ω-(1-H-1,2,4-triazol-1-yl)acetophenones [J].
Chu, CH ;
Sun, XW ;
Sun, L ;
Zhang, ZY ;
Li, ZC ;
Liao, RA .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1999, 46 (02) :229-232
[7]   1,2,4-TRIAZOLES .6. SYNTHESIS OF NEW 1,5-DIPHENYL-3-1H-1,2,4-TRIAZOLES SUBSTITUTED WITH H-, ALKYL, OR CARBOXYL GROUPS AT C-3 [J].
CZOLLNER, L ;
SZILAGYI, G ;
LANGO, J ;
JANAKY, J .
ARCHIV DER PHARMAZIE, 1990, 323 (04) :225-227
[8]   Highly efficient solvent-free synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones using tetrabutylammonium bromide as novel ionic liquid catalyst [J].
Davoodnia, A. ;
Allameh, S. ;
Fakhari, A. R. ;
Tavakoli-Hoseini, N. .
CHINESE CHEMICAL LETTERS, 2010, 21 (05) :550-553
[9]   SYNTHESIS AND ANTIFOLATE PROPERTIES OF 5,10-ETHANO-5,10-DIDEAZAAMINOPTERIN [J].
DEGRAW, JI ;
CHRISTIE, PH ;
COLWELL, WT ;
SIROTNAK, FM .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (02) :320-324
[10]  
Demirbs N., 2002, BIOORGAN MED CHEM, V10, P3723