Supported protic acid-catalyzed synthesis of 2,3-disubstituted thiazolidin-4-ones: enhancement of the catalytic potential of protic acid by adsorption on solid supports

Kumar, Dinesh; Sonawane, Mukesh Digambar; Pujala, Brahmam; Jain, Varun K.; Bhagat, Srikant; Chakraborti, Asit K.

doi:10.1039/c3gc41218k

Cited by 115 publications

(37 citation statements)

References 66 publications

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“…[36] Firstly, the imine formation via the condensation of 1 and amines 3a-d after that, the attack of the imine carbon by the sulfur moiety of the thioglycolic acid then intramolecular cyclization leading to the formation of thiazolidinone derivatives 4a-d (Scheme 2). It is assumed that the reaction may proceed via condensation-cyclization sequence.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of furo[3,2‐g]chromones under microwave irradiation and their antitumor activity evaluation

Abu‐Bakr

Khidre

Omar

et al. 2019

Journal of Heterocyclic Chem

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A series of furo[3,2-g]chromone derivatives were synthesized via the reaction of furochromone carbaldehyde 1 with amines 3a-d and thioglycolic acid to give thiazolidinones 4a-d. The later react with benzaldehyde/thiourea or hydroxylamine and DMF-DMA in glacial acetic acid to give thiazolopyrimidines 5a-d or thiazoloisoxazoles 6a-d, respectively. Also, the synthesis of α-aminophosphonates via the one-pot reaction of 1 and amines 3a,b were trapped by dialkylphosphites 7a-c afforded the corresponding αaminophosphonates 8a-f. Applying hexaalkyltriamidophosphites 9a,b to 1 gives alkylidenephosphorane ylides 11a,b in an open structure form. In the present investigation, the in vitro inhibition capacity of compounds (4a, 4c, 5b, 5c, 6b-d, 8a-f, and 11a) was screened in three human cancer cell lines HCT-116, MCF-7, and HepG2. The anticancer activity results revealed that 8b and 8e had more potent cytotoxic inhibition activity against HCT-116 cell line; however, all the tested compounds had obviously less cytotoxic activity against MCF-7 cell line, while 5b, 5c, and 6d were potent against HepG2 cell line compared with that of doxorubicin.

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Section: Resultsmentioning

confidence: 99%

Synthesis of furo[3,2‐g]chromones under microwave irradiation and their antitumor activity evaluation

Abu‐Bakr

Khidre

Omar

et al. 2019

Journal of Heterocyclic Chem

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“…催化剂 L3-Zn(OAc) 2 与巯基乙酸的羰基氧形成 O-Zn 键增加了羰基碳的亲电性, 促使分子内发生成环反应, 失去一份子水得到目标化合物 4-噻唑啉酮 [17,18] . 2,3-二苯基-4-噻唑啉酮(4a) [18] : 产率 88%, 黄色固体. m.p.…”

Section: 反应机理unclassified

One-Pot Synthesis of 4-Thiazolidinone Derivatives Catalyzed by Zinc Acetate-Schiff Base Complex Immobilized on Mesoporous Molecular Sieve MCM-41

邢雪建¹,

樊馗²,

庞海霞³

et al. 2016

Chin. J. Org. Chem.

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A new simple and efficient one-pot synthesis of thiazolidinone derivatives via aldehydes, amines and mercaptoacetic acid in the presence of Zn(OAc) 2 -Schiff base complex immobilized on MCM-41 is described. A variety of aldehydes and amines were engaged in the study and afforded respective thiazolidinones in high yield (up to 98%). Moreover, consistent activity of recovered catalyst was found to be almost same up to five cycles in 80% yield.

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“…In this context, recoverable and recyclable catalysts play a key role due to environmental and economical impacts. One of the promising routes to synthesize heterogeneous catalyst is to support the conventional catalyst on porous inorganic solids such as silica, alumina, titania, zirconia, zeolite, etc (Smith and Horwood, 1992;Kumar et al, 2013). Among different supported catalysts, silica supported catalysts have attracted considerable attention of chemists in recent years due to their large surface area, better selectivity, high mechanical and thermal stability, easy to handle, and long catalytic life which make it promising for both academic and industrial applications (Smith and Horwood, 1992;.…”

Section: Introductionmentioning

confidence: 99%

A convenient synthesis of coumarinyl chalcones using HClO4–SiO2: A green approach

Siddiqui

2019

Arabian Journal of Chemistry

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Graphical abstractA simple and efficient one-pot synthesis of coumarinyl chalcones was reported in the presence of silica supported perchloric acid under solvent-free heating at 80 °C in excellent yields. The catalyst was recycled for four runs without any loss of its catalytic activity. AbstractHClO 4 -SiO 2 catalysed synthesis of coumarinyl chalcones (8a-j) under solvent-free conditions is reported. The catalyst is characterized by powder XRD and SEM-EDX analysis. The stability of the catalyst is evaluated by thermogravimetric (TG) and differential scanning calorimetry (DSC) techniques. The remarkable features of this green protocol are excellent yields of the products, shorter reaction time, simple experimental procedure, easy preparation and reusability of the catalyst.

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Supported protic acid-catalyzed synthesis of 2,3-disubstituted thiazolidin-4-ones: enhancement of the catalytic potential of protic acid by adsorption on solid supports

Cited by 115 publications

References 66 publications

Synthesis of furo[3,2‐g]chromones under microwave irradiation and their antitumor activity evaluation

Synthesis of furo[3,2‐g]chromones under microwave irradiation and their antitumor activity evaluation

One-Pot Synthesis of 4-Thiazolidinone Derivatives Catalyzed by Zinc Acetate-Schiff Base Complex Immobilized on Mesoporous Molecular Sieve MCM-41

A convenient synthesis of coumarinyl chalcones using HClO4–SiO2: A green approach

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