Synthesis of 1, 8-dioxodecahydroacridines via Hantzsch condensation using theophylline in an aqueous medium: an eco-friendly and bio-based approach

被引:6
作者
Dhane, Nilam S. [1 ]
Sapkal, Aboli C. [2 ]
Attar, Suraj R. [2 ]
Dhumal, Sanchita M. [1 ]
Chougule, Ganesh K. [1 ]
Pawar, Samadhan P. [1 ]
Kamble, Santosh B. [2 ]
Gaikwad, Kishor V. [1 ]
机构
[1] Rajarshi Chhatrapati Shahu Coll, Kolhapur, India
[2] Karmaveer Bhaurao Patil Univ, Yashavantrao Chavan Inst Sci Satara, Lead Coll, Satara, India
关键词
Heterocycles; Eco-friendly and bio-based catalyst; 1; 8; Dioxodecahydroacridine; Aqueous medium; ONE-POT SYNTHESIS; HETEROGENEOUS CATALYST; ACRIDINE-DERIVATIVES; GREEN CATALYST; 1,8-DIOXODECAHYDROACRIDINES; EFFICIENT; ACID; HEXAHYDROQUINOLINES; NANOPARTICLES; NANOCATALYST;
D O I
10.1007/s11164-023-05213-1
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this work, we explored the convenient and sustainable method for the synthesis of 1, 8 dioxodecahydroacridine derivatives was achieved via a one-pot condensation reaction of dimedone, para-nitrobenzaldehyde, and ammonium acetate by using theophylline as a catalyst at room temperature in aqueous medium. This environmentally friendly method boasts several notable features, including high product yields, rapid completion of reactions, the use of eco-friendly and bio-based catalysts, straightforward work-up procedures without the need for column chromatography, cost-effectiveness, clean synthesis practices that avoid the use of harmful organic solvents, and exceptional atom efficiency.
引用
收藏
页码:1147 / 1160
页数:14
相关论文
共 52 条
[1]   A facile and efficient synthesis of 1,8-dioxodecahydroacridines derivatives catalyzed by cobalt-alanine metal complex under aqueous ethanol media [J].
Alam, M. Mujahid ;
Mubarak, Ahmed T. ;
Assiri, Mohammed A. ;
Ahmed, S. Merajuddin ;
Fouda, Ahmed M. .
BMC CHEMISTRY, 2019, 13 (1)
[2]   Combined experimental and computational study on Ag-NPs immobilized on rod-like hydroxyapatite for promoting Hantzsch reaction [J].
Amiri, Zahra ;
Malmir, Masoume ;
Hosseinnejad, Tayebeh ;
Kafshdarzadeh, Kosar ;
Heravi, Majid M. .
MOLECULAR CATALYSIS, 2022, 524
[3]   Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum [J].
Anderson, MO ;
Sherrill, J ;
Madrid, PB ;
Liou, AP ;
Weisman, JL ;
DeRisi, JL ;
Guy, RK .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (02) :334-343
[4]   Preparation of a novel magnetic bionanocomposite based on factionalized chitosan by creatine and its application in the synthesis of polyhydroquinoline, 1,4-dyhdropyridine and 1,8-dioxo-decahydroacridine derivatives [J].
Asgharnasl, Somayeh ;
Eivazzadeh-Keihan, Reza ;
Radinekiyan, Fateme ;
Maleki, Ali .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2020, 144 :29-46
[5]   Magnetic nanoparticle supported choline chloride-glucose (deep eutectic solvent) for the one-pot synthesis of 3,4-disubstituted isoxazol-5(4H)-ones [J].
Atharifar, Hengameh ;
Keivanloo, Ali ;
Maleki, Behrooz ;
Baghayeri, Mehdi ;
Alinezhad, Heshmatollah .
RESEARCH ON CHEMICAL INTERMEDIATES, 2024, 50 (01) :281-296
[6]   Synthesis of 1,8-Dioxo-decahydroacridine Derivatives via Ru- Catalyzed Acceptorless Dehydrogenative Multicomponent Reaction [J].
Biswas, Nandita ;
Srimani, Dipankar .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (14) :9733-9743
[7]   Amine-functionalized graphene oxide nanosheets (AFGONs): an efficient bifunctional catalyst for selective formation of 1,4-dihydropyridines, acridinediones and polyhydroquinolines [J].
Choudhury, Prasun ;
Ghosh, Pranab ;
Basu, Basudeb .
MOLECULAR DIVERSITY, 2020, 24 (01) :283-294
[8]   Amberlyst-15: An efficient reusable heterogeneous catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines [J].
Das, B ;
Thirupathi, P ;
Mahender, I ;
Reddy, VS ;
Rao, YK .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 247 (1-2) :233-239
[9]   A Rapid and Green Method for Solvent-Free Synthesis of 1,8-Dioxodecahydroacridines Using Tetrabutylammonium Hexatungstate as a Reusable Heterogeneous Catalyst [J].
Davoodnia, Abolghasem ;
Zare-Bidaki, Atefeh ;
Behmadi, Hossein .
CHINESE JOURNAL OF CATALYSIS, 2012, 33 (11) :1797-1801
[10]   Carbon-Based Solid Acid as an Efficient and Reusable Catalyst for the Synthesis of 1,8-Dioxodecahydroacridines Under Solvent-Free Conditions [J].
Davoodnia, Abolghasem ;
Khojastehnezhad, Amir ;
Tavakoli-Hoseini, Niloofar .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (07) :2243-2248