An Environmentally Benign Protocol for Aqueous Synthesis of Tetrahydrobenzo[b] Pyrans Catalyzed by Cost-Effective Ionic Liquid

被引:78
作者
Hu, Huanan [1 ,2 ]
Qiu, Fangli [1 ,2 ]
Ying, Anguo [1 ,2 ]
Yang, Jianguo [1 ,2 ]
Meng, Haiping [2 ]
机构
[1] Taizhou Univ, Inst Appl Chem, Taizhou 318000, Peoples R China
[2] Taizhou Univ, Sch Pharmaceut & Chem Engn, Taizhou 318000, Peoples R China
基金
中国国家自然科学基金;
关键词
pyran; choline hydroxide; ionic liquid; cost-effectiveness; biodegradability; recyclability; ONE-POT SYNTHESIS; SOLVENT-FREE CONDITIONS; EFFICIENT SYNTHESIS; VERSATILE CATALYST; ORGANIC-SYNTHESIS; ALPHA; BETA-UNSATURATED KETONES; KNOEVENAGEL CONDENSATION; MULTICOMPONENT REACTIONS; HETEROGENEOUS CATALYST; MICROWAVE IRRADIATION;
D O I
10.3390/ijms15046897
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A mild, efficient, and environmentally benign protocol for the synthesis of tetrahydrobenzo[b] pyran derivatives in the presence of readily accessible, biodegradable, and choline hydroxide based ionic liquid as catalyst has been established. The key features of the reported methodology include good to excellent yields of desired products, simple work-up procedure and good recyclability of catalysts, which may be a practical alternative to the existing conventional processes for the preparation of 4-H pyrans to cater to the requirements of academia as well as industry.
引用
收藏
页码:6897 / 6909
页数:13
相关论文
共 59 条
[1]   Supported choline hydroxide (ionic liquid) as heterogeneous catalyst for aldol condensation reactions [J].
Abelló, S ;
Medina, F ;
Rodríguez, X ;
Cesteros, Y ;
Salagre, P ;
Sueiras, JE ;
Tichit, D ;
Coq, B .
CHEMICAL COMMUNICATIONS, 2004, (09) :1096-1097
[2]   SYNTHESIS OF CYCLOBUTENES BY THE NOVEL PHOTOCHEMICAL RING CONTRACTION OF 4-SUBSTITUTED 2-AMINO-3,5-DICYANO-6-PHENYL-4H-PYRANS [J].
ARMESTO, D ;
HORSPOOL, WM ;
MARTIN, N ;
RAMOS, A ;
SEOANE, C .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3069-3072
[3]   (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
[4]   Tetra-methyl ammonium hydroxide:: An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media [J].
Balalaie, Saeed ;
Sheikh-Ahmadi, Masoumeh ;
Bararjanian, Morteza .
CATALYSIS COMMUNICATIONS, 2007, 8 (11) :1724-1728
[5]   Diammonium hydrogen phosphate:: An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media [J].
Balalaie, Saeed ;
Bararjanian, Morteza ;
Sheikh-Ahmadi, Masoumeh ;
Hekmat, Shohreh ;
Salehi, Peyman .
SYNTHETIC COMMUNICATIONS, 2007, 37 (7-9) :1097-1108
[6]   A green one-pot multicomponent synthesis of 4H-pyrans and polysubstituted aniline derivatives of biological, pharmacological, and optical applications using silica nanoparticles as reusable catalyst [J].
Banerjee, Subhash ;
Horn, Alissa ;
Khatri, Hari ;
Sereda, Grigoriy .
TETRAHEDRON LETTERS, 2011, 52 (16) :1878-1881
[7]   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
[8]   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
[9]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[10]  
Ellis G.P., 1977, Chromenes, chromanones, and chromones, DOI 10.1002/9780470187012