One-Pot Multicomponent Solvent-Free Synthesis of 2-Amino-4H-benzo[b]pyrans Catalyzed by Per-6-amino-β-cyclodextrin

被引:97
作者
Azath, Ismail Abulkalam [1 ]
Puthiaraj, Pillaiyar [1 ]
Pitchumani, Kasi [1 ]
机构
[1] Madurai Kamaraj Univ, Sch Chem, Madurai 625021, Tamil Nadu, India
关键词
Multicomponent reaction; Solvent-free synthesis; Aminocyclodextrin; Tetrahydrobenzo[b]pyrans; Supra molecular reusable catalyst; THROUGHPUT SCREENING ASSAY; APOPTOSIS INDUCERS; ENANTIOSELECTIVE SYNTHESIS; CONVENIENT SYNTHESIS; BETA-CYCLODEXTRIN; DERIVATIVES; DISCOVERY; SERIES; 4-ARYL-4H-CHROMENES; IRRADIATION;
D O I
10.1021/sc3000866
中图分类号
O6 [化学];
学科分类号
070301 [无机化学];
摘要
An efficient three-component reaction of aromatic aldehyde, 1,3-cyclohexanedione/dimedone, and malononitrile was developed, for the first time, using per-6-amino-beta-cyclodextrin, as a supramolecular host for aldehydes and an efficient base catalyst, which produced various substituted 2-amino-4H-benzo[b]pyrans in good to excellent yields, under solvent-free conditions. The catalyst can be reused at least three times without any marked change in its catalytic activity. Other remarkable features include a much milder procedure, a shorter reaction time, a wide range of functional group tolerance, and absence of any tedious workup or purification. This procedure also avoids hazardous reagents/solvents and is thus an eco-friendly alternative to the existing methods.
引用
收藏
页码:174 / 179
页数:6
相关论文
共 51 条
[1]
Alaa F. M., 2010, CHINESE J CHEM, V28, P91
[2]
Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2) [J].
Anderson, DR ;
Hegde, S ;
Reinhard, E ;
Gomez, L ;
Vernier, WF ;
Lee, L ;
Liu, S ;
Sambandam, A ;
Snider, PA ;
Masih, L .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (06) :1587-1590
[3]
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
[4]
Per-6-amino-β-cyclodextrin/CuI catalysed cyanation of aryl halides with K4[Fe(CN)6] [J].
Azath, Ismail Abulkalam ;
Suresh, Palaniswamy ;
Pitchumani, Kasi .
NEW JOURNAL OF CHEMISTRY, 2012, 36 (11) :2334-2339
[5]
(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
[6]
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[7]
2-A
[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]
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO