ZnO nanoparticles as a highly efficient heterogeneous catalyst for the synthesis of various chromene and pyrano[4,3-b]pyran derivatives under solvent-free conditions

被引:19
作者
Hossaini, Zinatossadat [1 ]
Sheikholeslami-Farahani, Fatemeh [2 ]
Soltani, Samira [1 ]
Sayyed-Alangi, S. Zahra [3 ]
Sajjadi-Ghotabadi, Hadi [3 ]
机构
[1] Islamic Azad Univ, Qaemshahr Branch, Dept Chem, Qaemshahr, Iran
[2] Islamic Azad Univ, Firoozkooh Branch, Dept Chem, Firoozkooh, Iran
[3] Islamic Azad Univ, Azadshahr Branch, Dept Chem, Azadshahr, Iran
关键词
aldehyde; chromene; ethyl cyanoacetate; malononitrile; pyrano[4,3-b]pyran; solvent-free reactions; three-component reactions; ANTIMICROBIAL EVALUATION; ANTIANAPHYLACTIC AGENTS; ANTIALLERGIC SUBSTANCES; CONVENIENT SYNTHESIS; CYCLIZATION; ALCOHOL; SURFACE; AMINES; SERIES; ALKYL;
D O I
10.1007/s10593-015-1654-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three- component reaction of 4-hydroxy-2H-pyran-2-one, aldehydes, and malononitrile or ethyl cyanoacetate in the presence of ZnO nanoparticles as the catalyst is described as an efficient and green synthetic method for obtaining of pyrano[4,3-b]pyran derivatives in excellent yield. These reactions were also tested with 2'-hydroxyacetophenone under similar conditions and produced chromene derivatives.
引用
收藏
页码:26 / 30
页数:5
相关论文
共 41 条
[1]   A CONVENIENT SYNTHESIS OF 1,3-DIARYL-1,2,3,4,-TETRAHYDRO-5,7,7-TRIMETHYL-4-OXO-2-THIOXO-7H-PYRANO[2,3-D]PYRIMIDINES [J].
AHLUWALIA, VK ;
KUMAR, R ;
KHURANA, A ;
BHATLA, R .
TETRAHEDRON, 1990, 46 (11) :3953-3962
[2]   Synthesis of Some New Heterocyclic Compounds Derived from 3-Formylchromones and Their Antimicrobial Evaluation [J].
Bari, A. ;
Ali, S. S. ;
Kadi, A. ;
Hashmi, I. A. ;
Ng, S. W. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 49 (12) :1723-1731
[3]   7-[3-(1-Piperidinyl)propoxy]chromenones as potential atypical antipsychotics [J].
Bolos, J ;
Gubert, S ;
Anglada, L ;
Planas, JM ;
Burgarolas, C ;
Castello, JM ;
Sacristan, A ;
Ortiz, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (15) :2962-2970
[4]   PYRIDO[2,3-D]PYRIMIDINES .4. SYNTHETIC STUDIES LEADING TO VARIOUS OXOPYRIDO[2,3-D]PYRIMIDINES [J].
BROOM, AD ;
SHIM, JL ;
ANDERSON, GL .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (07) :1095-1099
[5]  
Chauder BA, 1998, SYNTHESIS-STUTTGART, P279
[6]   Control of uniform nanostructured α-Ni(OH)2 with self-assembly sodium dodecyl sulfate templates [J].
Cheng, Ming-Yao ;
Hwang, Bing-Joe .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2009, 337 (01) :265-271
[7]   UV-induced photocatalytic degradation of azo dyes by organic-capped ZnO nanocrystals immobilized onto substrates [J].
Comparelli, R ;
Fanizza, E ;
Curri, ML ;
Cozzoli, PD ;
Mascolo, G ;
Agostiano, A .
APPLIED CATALYSIS B-ENVIRONMENTAL, 2005, 60 (1-2) :1-11
[8]   4'-HYDROXY-3-METHOXYFLAVONES WITH POTENT ANTIPICORNAVIRUS ACTIVITY [J].
DEMEYER, N ;
HAEMERS, A ;
MISHRA, L ;
PANDEY, HK ;
PIETERS, LAC ;
VANDENBERGHE, DA ;
VLIETINCK, AJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :736-746
[9]   BENZOPYRONES .14. SYNTHESIS AND ANTI-ALLERGIC PROPERTIES OF SOME N-TETRAZOLYLCARBOXAMIDES AND RELATED COMPOUNDS [J].
ELLIS, GP ;
BECKET, GJP ;
SHAW, D ;
WILSON, HK ;
VARDEY, CJ ;
SKIDMORE, IF .
JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (11) :1120-1126
[10]  
Foye W.O., 1991, PRINICIPI CHIMICA FA, P416, DOI DOI 10.1021/cr2000459