Quick synthesis of isatin-derived knoevenagel adducts using only eco-friendly solvent

被引：10

作者：

Gomes de Oliveira Ferreira, Joao Marcos ^{[1
]}

da Silva, Girlyanderson Araujo ^{[1
]}

Coelho, Maisa Cavalcanti ^{[1
]}

Lima Junior, Claudio Gabriel ^{[1
]}

Vale, Juliana Alves ^{[1
]}

机构：

[1] Univ Fed Paraiba, Dept Quim, BR-58051970 Joao Pessoa, Paraiba, Brazil

来源：

RESULTS IN CHEMISTRY | 2021年 / 3卷

关键词：

Knoevenagel condensation; Binary mixture; Isatin; CYCLIC 2-OXINDOLE DERIVATIVES; ANTIMICROBIAL EVALUATIONS; HETEROCYCLIC-COMPOUNDS; IONIC LIQUID; CONDENSATION; CATALYST;

D O I：

10.1016/j.rechem.2021.100135

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A variety of knoevenagel compounds from isatin were synthesized using an eco-friendly methodology. It was used only the binary solvent ethanol: water (3:7 v/v) without the presence of metal catalyst what enabled the reaction between different isatins with malononitrile in a quick reaction time of 2-5 min and isolated yields 80-96%. When cyanoesters were used as methylene actives, the reactions were longer and the knoenevagel products were obtained 79-92% isolated yields.

引用

页数：6

共 45 条

[1] Isatin-benzoazine molecular hybrids as potential antiproliferative agents: synthesis and in vitro pharmacological profiling [J].

Abdel-Aziz, Hatem A. ;

Eldehna, Wagdy M. ;

Keeton, Adam B. ;

Piazza, Gary A. ;

Kadi, Adnan A. ;

Attwa, Mohamed W. ;

Abdelhameed, Ali S. ;

Attia, Mohamed I. .

DRUG DESIGN DEVELOPMENT AND THERAPY, 2017, 11 :2333-2346

[2] Organocatalyzed domino reactions: diversity oriented synthesis of pyran-annulated scaffolds using in situ-developed benzylidenemalononitriles [J].

Ahad, Abdul ;

Farooqui, Maqdoom .

RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (04) :2445-2455

[3] New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] Derivatives [J].

Auria-Luna, Fernando ;

Marques-Lopez, Eugenia ;

Mohammadi, Somayeh ;

Heiran, Roghayeh ;

Herrera, Raquel P. .

MOLECULES, 2015, 20 (09) :15807-15826

[4] Ionic Liquid Mediated Green Synthesis of Spirooxindoles from N-methyl Quinolones and Their Anti Bacterial Activity [J].

Bhupathi, Raja S. ;

Madhu, Bandi ;

Reddy, Ch. Venkata Ramana ;

Devi, B. Rama ;

Dubey, P. K. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (04) :2326-2332

[5] REVIEW OF SYNTHESIS OF SPIRO HETEROCYCLIC COMPOUNDS FROM ISATIN [J].

Borad, Mayuri A. ;

Bhoi, Manoj N. ;

Prajapati, Neelam P. ;

Patel, Hitesh D. .

SYNTHETIC COMMUNICATIONS, 2014, 44 (07) :897-922

[6] Review of Synthesis of Multispiro Heterocyclic Compounds from Isatin [J].

Borad, Mayuri A. ;

Bhoi, Manoj N. ;

Prajapati, Neelam P. ;

Patel, Hitesh D. .

SYNTHETIC COMMUNICATIONS, 2014, 44 (08) :1043-1057

[7] A Simple and Efficient Protocol for the Knoevenagel Reaction of Benzylidenemalononitriles and the Evaluation of the Larvicidal Activity on Aedes Aegypti [J].

Carvalho, Harlyson L. ;

de Amorim, Andreia L. ;

Araujo, Inana F. ;

Marino, Bianca L. B. ;

Jimenez, David E. Q. ;

Ferreira, Ricardo M. A. ;

Hage-Melim, Lorane I. S. ;

Souto, Raimundo N. P. ;

Porto, Andre L. M. ;

Ferreira, Irlon M. .

REVISTA VIRTUAL DE QUIMICA, 2018, 10 (02) :362-374

[8] Isatin-1,2,3-triazole-isatin Scaffolds and Their Antibacterial Activity [J].

Cheng, Ruijing ;

Yan, Xinjia ;

Xu, Zhi .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (10) :2970-2974

[9] Discovery of a new class of potent, selective, and orally bioavailable CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases [J].

Crosignani, Stefano ;

Page, Patrick ;

Missotten, Marc ;

Colovray, Veronique ;

Cleva, Christophe ;

Arrighi, Jean-Francois ;

Atherall, John ;

Macritchie, Jackie ;

Martin, Thierry ;

Humbert, Yves ;

Gaudet, Marilene ;

Pupowicz, Doris ;

Maio, Maurizio ;

Pittet, Pierre-Andre ;

Golzio, Lucia ;

Giachetti, Claudio ;

Rocha, Cynthia ;

Bernardinelli, Gerald ;

Filinchuk, Yaroslav ;

Scheer, Alexander ;

Schwarz, Matthias K. ;

Chollet, Andre .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (07) :2227-2243

[10] Multicomponent Reactions in the Synthesis of Complex Fused Coumarin Derivatives [J].

da Silveira Pinto, Ligia S. ;

Couri, Mara R. C. ;

de Souza, Marcus V. N. .

CURRENT ORGANIC SYNTHESIS, 2018, 15 (01) :21-37

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