Tetra-methyl ammonium hydroxide:: An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media

被引:182
作者
Balalaie, Saeed [1 ]
Sheikh-Ahmadi, Masoumeh [1 ]
Bararjanian, Morteza [1 ]
机构
[1] KN Toosi Univ Technol, Peptide Res Grp, Tehran, Iran
关键词
4H-Benzo[b]pyrans; 4H-Chromene; tetra-methyl ammonium hydroxide; aqueous media; Tandem Knoevenagel-cyclocondensation reaction;
D O I
10.1016/j.catcom.2007.01.034
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
Tetra-methyl ammonium hydroxide has been used as a mild, efficient, neutral and cheap catalyst for the synthesis of various 4H-benzo[b]pyran derivatives via a one-pot three-component condensation in aqueous media. This method offers the advantages of proceeding, neutral and mild conditions, giving high to excellent yields of the products and simple work-up. (c) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:1724 / 1728
页数:5
相关论文
共 24 条
[1]  
Andreani L.L., 1960, BOLL CHIM FARM, V99, P583
[2]  
[Anonymous], CHEM ABSTR
[3]  
Arnesto D, 1989, J ORG CHEM, V54, P3069
[4]   (S)-Proline as a neutral and efficient catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media [J].
Balalaie, S ;
Bararjanian, M ;
Amani, AM ;
Movassagh, B .
SYNLETT, 2006, (02) :263-266
[5]   An efficient one-pot synthesis of 6-aryl-5-cyano-2-thiopyrimidinone derivatives and their piperidinium ionic forms, X-ray crystal structures [J].
Balalaie, Saeed ;
Bararjanian, Morteza ;
Rominger, Frank .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (04) :821-826
[6]   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
[7]   Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions [J].
Devi, I ;
Bhuyan, PJ .
TETRAHEDRON LETTERS, 2004, 45 (47) :8625-8627
[8]   Ionic liquid promoted Knoevenagel and Michael reactions [J].
Fan, XS ;
Hu, XY ;
Zhang, XY ;
Wang, JJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2004, 57 (11) :1067-1071
[9]  
Gonzalez R., 1985, J CHEM SOC P1, P1202
[10]  
Green G.R., 1995, Comprehensive Heterocyclic Chemistry II, VVol. 5, P469, DOI DOI 10.1016/B978-008096518-5.00112-X