Catalyst-free, one-pot expeditious synthesis of polyhydroquinolines and 2-amino-4H-chromenes

被引:6
作者
Ganwir, Prerna [1 ]
Bandivadekar, Priyanka [1 ]
Kudale, Pawan [1 ]
Chaturbhuj, Ganesh U. [1 ]
机构
[1] Inst Chem Technol, Dept Pharmaceut Sci & Technol, Mumbai 400019, Maharashtra, India
关键词
Polyhydroquinolines; Chromene; Dimedone; Multicomponent; Catalyst-free; SOLVENT-FREE CONDITIONS; SULFATED POLYBORATE; EFFICIENT CATALYST; MULTICOMPONENT SYNTHESIS; DIHYDROPYRIDINE HYBRIDS; HETEROGENEOUS CATALYST; ENVIRONMENTALLY BENIGN; BIOLOGICAL EVALUATION; ANTICANCER ACTIVITY; REUSABLE CATALYST;
D O I
10.1007/s11164-022-04763-0
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The present work highlights a rapid, efficient, eco-friendly protocol for synthesizing one-pot polyhydroquinolines via Hantzsch reaction and 2-amino-4H-chromene derivatives under catalyst-free condition. The present mild and greener method uses ethanol: water (1:1) without catalyst at R.T. and 90 degrees C. The structurally diverse substrates were selected to ascertain the ability of the current approach to handle different functional groups, including ketones as one of the substrates. The current methodology is economical and environmentally friendly for the three and four-component reaction of aliphatic, acyclic, aromatic, heterocyclic aldehydes in shorter reaction time, simple workup procedure, no catalyst with excellent yields, and high atom efficiency are the added advantages of this protocol. [GRAPHICS] .
引用
收藏
页码:3429 / 3447
页数:19
相关论文
共 100 条
[1]  
Abaszadeh M, 2015, RES CHEM INTERMEDIAT, V41, P5229, DOI 10.1007/s11164-014-1624-7
[2]   A novel QSAR model for predicting induction of apoptosis by 4-aryl-4H-chromenes [J].
Afantitis, Antreas ;
Melagraki, Georgia ;
Sarimveis, Haralambos ;
Koutentis, Panayiotis A. ;
Markopoulos, John ;
Igglessi-Markopoulou, Olga .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (19) :6686-6694
[3]   Mo@GAA-Fe3O4 MNPs: a highly efficient and environmentally friendly heterogeneous magnetic nanocatalyst for the synthesis of polyhydroquinoline derivatives [J].
Aghaei-Hashjin, Mehraneh ;
Yahyazadeh, Asieh ;
Abbaspour-Gilandeh, Esmayeel .
RSC ADVANCES, 2021, 11 (18) :10497-10511
[4]   Chitosan Decorated Copper Nanoparticles as Efficient Catalyst for Synthesis of Novel Quinoline Derivatives [J].
Alghamdi, K. S. ;
Ahmed, N. S. I. ;
Bakhotmah, D. ;
Mokhtar, M. .
JOURNAL OF NANOSCIENCE AND NANOTECHNOLOGY, 2020, 20 (02) :890-899
[5]  
Arce G., 2015, WORLD J CHEM ED, V3, P27, DOI [10.12691/wjce-3-1-4, DOI 10.12691/WJCE-3-1-4]
[6]   One-step, synthesis of Hantzsch esters and polyhydroquinoline derivatives using new organocatalyst [J].
Baghbanian, Seyed Meysam ;
Khaksar, Samad ;
Vahdat, Seyed Mohammad ;
Farhang, Maryam ;
Tajbakhsh, Mahmood .
CHINESE CHEMICAL LETTERS, 2010, 21 (05) :563-567
[7]   (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
[8]   In situ synthesis of SO3H supported Fe3O4@resorcinol-formaldehyde resin core/shell and its catalytic evaluation towards the synthesis of hexahydroquinoline derivatives in green conditions [J].
Barzkar, Aliyeh ;
Beni, Alireza Salimi .
RSC ADVANCES, 2020, 10 (68) :41703-41712
[9]   Antitumor agents. 3. Design, synthesis, and biological evaluation of new pyridoisoquinolindione and dihydrothienoquinolindione derivatives with potent cytotoxic activity [J].
Bolognese, A ;
Correale, G ;
Manfra, M ;
Lavecchia, A ;
Mazzoni, O ;
Novellino, E ;
La Colla, P ;
Sanna, G ;
Loddo, R .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (04) :849-858
[10]   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