Titanium dioxide nanoparticles as efficient catalyst for the synthesis of pyran's annulated heterocyclic systems via three-component reaction

被引:14
作者
Edjlali, Ladan [1 ]
Khanamiri, Rahim Hosseinzdeh [1 ]
机构
[1] Islamic Azad Univ, Tabriz Branch, Dept Chem, Tabriz, Iran
来源
MONATSHEFTE FUR CHEMIE | 2016年 / 147卷 / 07期
关键词
Titanium dioxide; Pyran; Pyrimidine; Green chemistry; Nanoparticle; DERIVATIVES;
D O I
10.1007/s00706-015-1624-3
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Titanium dioxide nanoparticles were introduced as a new and efficient heterogeneous catalyst for the synthesis of pyran's annulated heterocyclic systems via three-component reaction. The reaction was carried out between various aldehydes, malononitrile, and cyclic CH-acids in H2O as a green solvent at 50 A degrees C during 10 h. This reaction gave pyrans containing heterocyclic compounds including nineteen derivatives in good yields. Titanium dioxide nanoparticles were recycled and reused for six times without significant decrease in the catalyst amount and efficiency. This approach is very efficient, economical, and environmentally benign process since titanium dioxide is a cheap, available, non-toxic, and recyclable catalyst. [GRAPHICS]
引用
收藏
页码:1221 / 1225
页数:5
相关论文
共 23 条
[1]   Nanozeolite clinoptilolite as a highly efficient heterogeneous catalyst for the synthesis of various 2-amino-4H-chromene derivatives in aqueous media [J].
Baghbanian, Seyed Meysam ;
Rezaei, Niloufar ;
Tashakkorian, Hamed .
GREEN CHEMISTRY, 2013, 15 (12) :3446-3458
[2]   SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 2-OXO-(2H) 1-BENZOPYRAN-3-CARBOXAMIDE DERIVATIVES [J].
BONSIGNORE, L ;
LOY, G ;
SECCI, D ;
CALIGNANO, A .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (06) :517-520
[3]   Bifunctional nanocrystalline MgO for chiral epoxy ketones via Claisen-Schmidt condensation-asymmetric epoxidation reactions [J].
Choudary, BM ;
Kantam, ML ;
Ranganath, KVS ;
Mahendar, K ;
Sreedhar, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3396-3397
[4]  
Coates WJ, 1990, Eur Pat, Patent No. 351058
[5]   ANTIMALARIAL SUBSTANCES .26. FOLATE ANTAGONISTS .4. ANTIMALARIAL AND ANTIMETABOLITE EFFECTS OF 2,4-DIAMINO-6-[(BENZYL)AMINO]PYRIDO[2,3-D]-PYRIMIDINES [J].
DAVOLL, J ;
CLARKE, J ;
ELSLAGER, EF .
JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (08) :837-&
[6]   The Regiospecific Synthesis of Some New 3,5-Disubstituted Isoxazoles [J].
Edjlali, Ladan .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2008, 55 (06) :1322-1325
[7]  
Fenn D., 1994, PYRIMIDINES
[8]   HETEROGENEOUS CATALYSIS - INTRODUCTION [J].
GEORGE, SM .
CHEMICAL REVIEWS, 1995, 95 (03) :475-476
[9]   Synthesis and antibacterial properties of new dithienyl containing pyran, pyrano[2,3-b] pyridine, pyrano[2,3-d]pyrimidine and pyridine derivatives [J].
Ghorab, MM ;
Hassan, AY .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1998, 141 :251-261
[10]  
Grieco P.A., 1998, Organic Synthesis in Water