Highly efficient synthesis of coumarin derivatives in the presence of H14[NaP5W30O110] as a green and reusable catalyst

被引:87
作者
Heravi, Majid M. [1 ]
Khorasani, Marzieh
Derikvand, Faterneh
Oskoole, Hossein A.
Bamoharrarn, Fatemeh F.
机构
[1] Alzahra Univ, Sch Sci, Dept Chem, Tehran, Iran
[2] Islamic Azad Univ, Dept Chem, Mashhad Branch, Mashhad, Iran
关键词
coumarin heteropolyacid; preyssler catalyst; pechmann;
D O I
10.1016/j.catcom.2007.02.030
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A variety of heteropolyanions including: Keggin, Dawson, Preyssler, mixed addenda and sandwich types, catalyzed the formation of 4-methylnaphtho-(1,2-b)-pyran-2-one (coumarin) from the condensation of a-naphthol and ethylacetoacetate in a solvent free system and under heating conditions. Our data vividly indicate that sodium30-tungsto pentaphosphate, [NaP5W30O110](14-), which so-called Preyssler's anion, with high hydrolytic (pH 0-12) and thermal stability is the catalyst of choice. This catalyst catalyzed the synthesis of other coumarin derivatives in high yields and good selectivity. (c) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:1886 / 1890
页数:5
相关论文
共 42 条
[1]   Bismuth(III) nitrate pentahydrate - a mild and inexpensive reagent for synthesis of coumarins under mild conditions [J].
Alexander, VM ;
Bhat, RP ;
Samant, SD .
TETRAHEDRON LETTERS, 2005, 46 (40) :6957-6959
[2]  
[Anonymous], LASER DYES
[3]  
[Anonymous], 1884, CHEM BER
[4]   Catalytic performance of Preyssler heteropolyacid as a green and recyclable catalyst in oxidation of primary aromatic amines [J].
Bamoharram, Fatemeh F. ;
Heravi, Majid M. ;
Roshani, Mina ;
Akbarpour, Mina .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 255 (1-2) :193-198
[5]   N-oxidation of pyridine carboxylic acids using hydrogen peroxide catalyzed by a green heteropolyacid catalyst:: Preyssler's anion, [NaP5W30O110]14- [J].
Bamoharram, Fatemeh F. ;
Heravi, Majid M. ;
Roshani, Mina ;
Tavakoli, Niloofar .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 252 (1-2) :219-225
[6]   Preyssler catalyst,[NaP5W30O110]14- :: A green, efficient and reusable catalyst for esterification of salicylic acid with aliphatic and benzylic alcohols [J].
Bamoharram, FF ;
Heravi, MM ;
Roshani, M ;
Jahangir, M ;
Gharib, A .
APPLIED CATALYSIS A-GENERAL, 2006, 302 (01) :42-47
[7]   THE DETERMINATION OF PORE VOLUME AND AREA DISTRIBUTIONS IN POROUS SUBSTANCES .1. COMPUTATIONS FROM NITROGEN ISOTHERMS [J].
BARRETT, EP ;
JOYNER, LG ;
HALENDA, PP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (01) :373-380
[8]   Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the knoevenagel synthesis of coumarin-3-carboxylic acids [J].
Bigi, F ;
Chesini, L ;
Maggi, R ;
Sartori, G .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1033-1035
[9]   Improved synthesis of some hydroxycoumarins [J].
Bulut, M ;
Erk, C .
DYES AND PIGMENTS, 1996, 30 (02) :99-104
[10]   Synthesis of coumarins by flash vacuum pyrolysis of 3-(2-hydroxyaryl)propenoic esters [J].
Cartwright, GA ;
McNab, H .
JOURNAL OF CHEMICAL RESEARCH-S, 1997, (08) :296-297