5688-82-4Relevant articles and documents
Facile synthesis of 3,4-fused tricyclic indoles with a seven-membered ring through a three-component reaction of 4-hydroxyindole, aldehyde, and malonodinitrile or ethyl cyanoacetate
Bai, Rongxian,Yang, Jian,Min, Lijun,Liu, Changhui,Wu, Fengtian,Gu, Yanlong
, p. 2170 - 2177 (2016)
Three-component reactions of 4-hydroxyindole, aldehydes, and malonodinitrile or ethyl cyanoacetate were developed for the first time by using either potassium fluoride or diethylamine as a catalyst, which provided an easy access to 3,4-fused tricyclic indoles in good to excellent yield. The merits of this synthesis route are attributed to its simplicity, practicality, efficiency, and eco-friendliness, as well as the easy availability of the catalyst.
New insights into the exploitation of oxidized carbon nitrides as heterogeneous base catalysts
Criado, Alejandro,Filippini, Giacomo,Fornasiero, Paolo,Gentile, Giuseppe,Gombac, Valentina,Melchionna, Michele,Prato, Maurizio,Rosso, Cristian
supporting information, (2021/12/08)
In this work, the development of a novel efficient heterogeneous catalytic system capable of driving Knoevenagel condensation reactions between benzaldehydes and malononitrile was reported. Specifically, we explored a post-synthetic modification of graphitic carbon nitride (g-CN) through a strong oxidation treatment by acid mixture (HNO3/H2SO4). The as-prepared oxidized CN material (CNO) shows a large number of surface acidic moieties, that can be easily deprotonated through an aqueous alkaline wash with different bases (NaOH, K2CO3, t-BuOK), to introduce a high density of reactive basic sites. The best catalyst is obtained with NaOH as the base (CNO-NaOH), and displays high reactivity and good tolerance towards functional group variations of the reagents, thus emerging as a potential new recyclable carbon nitride-based structure for organic base catalysis.
Synthesis of 5H-indeno[1,2-b]pyridine derivatives: Antiproliferative and antimetastatic activities against two human prostate cancer cell lines
Charris, Katiuska E.,Rodrigues, Juan R.,Ramírez, Hegira,Fernandez-Moreira, Esteban,ángel, Jorge E.,Charris, Jaime E.
, (2021/05/07)
This study describes the direct synthesis of 2-amino-4-(phenylsubstituted)-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives 5–21, through sequential multicomponent reaction of aromatic aldehydes, malononitrile, and 1-indanone in the presence of ammonium acetate and acetic acid (catalytic). The biological study showed that compound 10 significantly impeded proliferation of the cell lines PC-3, LNCaP, and MatLyLu. The antimetastatic effects of compound 10 could be related with inhibition of MMP9 in the PC-3 and LNCaP human cell lines. On the basis of a study of the structure–activity relationship of these compounds, we propose that the presence of two methoxy groups at positions 6 and 7 of the indeno nucleus and a 4-hydroxy-3-methoxy phenyl substitution pattern at position 4 of the pyridine ring is decisive for these types of molecules to exert?very good antiproliferative and antimetastatic activities.