TBAHS-Catalyzed Simple and Eco-friendly Protocol for the Synthesis of Novel Bioactive 2-Amino-4-aryl-5-oxo-5,6,7,8-tetrahydro-4H-chromene Derivatives

被引：0

作者：

Rakhe, S. D. ^{[1
]}

Mahurkar, S. S. ^{[1
]}

More, R. A. ^{[2
]}

Deshmukh, A. V. ^{[1
]}

Kamale, B. D. ^{[1
]}

Angulwar, J. A. ^{[1
]}

机构：

[1] Dayanand Sci Coll, Dept Chem, Latur 413512, India

[2] Dayanand Sci Coll, Dept Microbiol, Latur 413512, India

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 60卷 / 04期

关键词：

cyclohexane-1,3-dione; malononitrile; aromatic aldehydes; TBAHS; multicomponent reaction (MCR); 2-amino-4H-chromene; POT MULTICOMPONENT SYNTHESIS; EFFICIENT; GREEN; INHIBITORS;

D O I：

10.1134/S1070428024040225

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An effective environmentally friendly procedure has been proposed for the synthesis of novel bioactive 2-amino-4H-chromene derivatives by one-pot three-component condensation of aromatic aldehydes, malononitrile, and cyclohexane-1,3-dione using tetrabutylammonium hydrogen sulfate (TBAHS) as a catalyst under reflux conditions. The product structure was confirmed by IR, H-1 and C-13 NMR, and mass spectroscopic techniques. Simple workup procedure, excellent yields, and short reaction times are the most attractive benefits of the proposed multicomponent approach.

引用

页码：723 / 727

页数：5

共 29 条

[1] Angulwar JA, 2018, HETEROCYCL LETT, V8, P213
[2] Graphene Oxide Functionalized Organic-Inorganic Hybrid (GO-Si-NH2-PMo): An Efficient and Green Catalyst for the Synthesis of Tetrahydrobenzo[b]pyran Derivatives
Ataie, Farideh
Davoodnia, Abolghasem
Khojastehnezhad, Amir
[J]. POLYCYCLIC AROMATIC COMPOUNDS, 2021, 41 (04) : 781 - 794
[3] Tetra-methyl ammonium hydroxide:: An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media
Balalaie, Saeed
Sheikh-Ahmadi, Masoumeh
Bararjanian, Morteza
[J]. CATALYSIS COMMUNICATIONS, 2007, 8 (11) : 1724 - 1728
[4] Efficient entry to trifluoromethyl substituted chromanes from oxidative aromatization of tetrahydro-2H-chromen-5(6H)-ones using iodine/alcohol with conventional and microwave methods
Bonacorso, Helio G.
Navarini, Jussara
Wiethan, Carson W.
Junges, Andrizia F.
Cavinatto, Susiane
Andrighetto, Rosalia
Martins, Marcos A. P.
Zanatta, Nilo
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2012, 142 : 90 - 95
[5] Coumarins derivatives as dual inhibitors of acetylcholinesterase and monoamine oxidase
Brühlmann, C
Ooms, F
Carrupt, PA
Testa, B
Catto, M
Leonetti, F
Altomare, C
Carotti, A
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (19) : 3195 - 3198
[6] Cheap thiamine hydrochloride as efficient catalyst for synthesis of 4H-benzo[b]pyrans in aqueous ethanol
Chen, Lu
Bao, Sunan
Yang, Lixiang
Zhang, Xian
Li, Bin
Li, Yibiao
[J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (07) : 3883 - 3891
[7] Synthesis of 2-Amino-4H-chromene Derivatives Using InCl3 and Their Antimicrobial Evaluation
Choudhare, S. S.
Bhosale, V. N.
Chopade, M.
[J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 58 (06) : 913 - 916
[8] Biological importance of structurally diversified chromenes
Costa, Marta
Dias, Tatiana A.
Brito, Alexandra
Proenca, Fernanda
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 123 : 487 - 507
[9] Multi-component syntheses of heterocycles by transition-metal catalysis
D'Souza, Daniel M.
Mueller, Thomas J. J.
[J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1095 - 1108
[10] A novel synthesis of dibenzo[c,f]chromenes, dibenzo[c,h]chromenes and benzo[7,8]chromeno[3,4-f]isoindoles as antimicrobial agents
El-Gaby, MSA
Zahran, MA
Ismail, MMF
Ammar, YA
[J]. FARMACO, 2000, 55 (03): : 227 - 232

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