Tetrabutylammonium Hydrogen Sulfate mediated Three-Component Reaction for the Synthesis of Thiadiazolo [2,3-b] Quinazolin-6-(7H)-ones and Antioxidant Activity

Khansole, Gopinath S.; Prasad, Divya; Angulwar, Jaman A.; Atar, Amol B.; Nagaraja, Bhari Mallanna; Patil, Komal; Bhosale, Vijay N.

doi:10.1016/j.matpr.2018.10.389

Cited by 4 publications

(3 citation statements)

References 10 publications

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“…The multicomponent synthesis of thiadiazolo[2,3-b]quinazolin-6-(7H)-ones 81 could be accomplished from 2-amino-5-phenyl-1,3,4-thiadiazoles 80, aromatic aldehydes 1 and dimedone (10a) in the presence of catalytic amounts of tetrabutylammonium hydrogen sulfate (Bu 4 NHSO 4 ) in ethanol-water (1:1) under refluxing conditions (Scheme 34). Besides, this study showed that thiadiazolo[2,3-b]quinazolin-6-(7H)-ones 81 could be formed with high atom-economy involving the formation of one C-C and two C-N bonds in only one step [77]. The antioxidant activity of the synthesized compounds was screened by DPPH and OH radical scavenging assays using ascorbic acid as reference compound.…”

Section: Antioxidant Activitymentioning

confidence: 98%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review.Molecules 2020, 25, 505 2 of 71 acetylcholinesterase inhibitors, anti-HIV, antimicrobial, antioxidant, anti-mycobacterial and anticancer activities ( Figure 1). It is noteworthy that 64% and 16% of the supporting literature found for this review correspond to heterocyclic structures with anticancer and antimicrobial activities, respectively. Scheme 2. Three-component synthesis of 3,4-dihydropyrimidinones/thiones type 7 under microwave irradiation, for anti-inflammatory activity.Patil et al., reported a one-pot pseudo-five-component synthesis of highly functionalized tetrahydropyridines 9 using Cu(OTf) 2 as catalyst, Scheme 3. In vitro anti-inflammatory activity of the obtained compounds 9 was determined against matrix metalloproteinases (MMPs) as MMP-2 and MMP-9 by using gelatin zymography [29]. Scheme 3. Multicomponent Cu(OTf) 2 catalyzed synthesis of substituted tetrahydropyridines 9 for anti-inflammatory activity.A highly diastereoselective synthesis (exclusively the cis isomer is formed), of chromeno β-lactam hybrids 13/14 was also achieved by an efficient one-pot three-component reaction between either 5,5-dimethylcyclohexane-1,3-dione (10a) or 4-hydroxycoumarin (10b), diverse benzaldehydes 11 and malononitrile (12), in the presence of DABCO under reflux conditions (Scheme 4). Scheme 4. Three-component synthesis of β-lactam hybrids 13/14 for anti-inflammatory activity.The synthesized compounds (13 in 80-95% yield) and (14 in 82-95% yield) were screened for anti-inflammatory activity (as well as for anticancer activity, please see Section 3.13.13. Compound 13b (Ar = 4-ClC 6 H 4 , Ar 1 = 4-MeC 6 H 4 ) was the most active of all the chromeno β-lactam hybrids 13/14 tested, with a 19.8 anti-inflammatory ratio, although, it resulted less active than the reference drug dexamethasone corticosteroid used for the treatment of rheumatoid and skin inflammation [30].

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Section: Antioxidant Activitymentioning

confidence: 98%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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“…Thiadiazoloquinazolinones 163 can also be prepared from diketones 33, aldehydes 2, and thiadiazoloamines 162 as nitrogen sources, by an on-water microwave-assisted reaction catalyzed by p-toluen sulfonic acid. Notably, not only do aromatic aldehydes work well in this process, but formaldehyde or acetaldehyde work as well (Scheme 70) [149]; this reaction with aromatic aldehydes has also been performed in water-ethanol mixture with tetrabutylammonium hydrogen sulfate as the catalyst, and some of the thiadiazoloquinazolinones obtained showed potent antioxidant activity [150]. The synthesis of benzimidazoloquinazolinones 161 can be promoted by heterogeneous Fe 3 O 4 @chitosan as a superparamagnetic nanocatalyst, under mild reaction conditions, using 2-aminobenzimidazole or 2-aminobenzothiazole 152 as nitrogen source, dimedone 33 and aromatic aldehydes 2 (Scheme 69) [148].…”

Section: Modification Of Two Componentsmentioning

confidence: 99%

Section: Modification Of Two Componentsmentioning

confidence: 99%

Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions

et al. 2022

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The interest in 3,4-dihydropyrimidine-2(1H)-(thio)ones is increasing every day, mainly due to their paramount biological relevance. The Biginelli reaction is the classical approach to reaching these scaffolds, although the product diversity suffers from some limitations. In order to overcome these restrictions, two main approaches have been devised. The first one involves the modification of the conventional components of the Biginelli reaction and the second one refers to the postmodification of the Biginelli products. Both strategies have been extensively revised in this manuscript. Regarding the first one, initially, the modification of one of the components was covered. Although examples of modifications of the three of them were described, by far the modification of the keto ester counterpart was the most popular approach, and a wide variety of different enolizable carbonylic compounds were used; moreover, changes in two or the three components were also described, broadening the substitution of the final dihydropyrimidines. Together with these modifications, the use of Biginelli adducts as a starting point for further modification was also a very useful strategy to decorate the final heterocyclic structure.

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Efficient synthesis of novel thiadiazolo[2,3-b]quinazolin-6-ones catalyzed by diphenhydramine hydrochloride-CoCl2⋅6H2O deep eutectic solvent

Korbekandi,

Mohammadpoor-Baltork,

Moghadam

et al. 2024

Sci Rep

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In this research, a new Lewis acid-based deep eutectic solvent (LA-DES) was synthesized using diphenhydramine hydrochloride and CoCl2·6H2O, (2[HDPH]:CoCl42−), and identified by FT-IR and 1HNMR techniques. The physicochemical properties of this LA-DES, such as thermal behavior, thermal stability, and solubility in common solvents were also investigated. The catalytic ability of 2[HDPH]:CoCl42− was ascertained in the efficient synthesis of a novel array of thiadiazolo[2,3-b]quinazolin-6-one scaffolds via a one-pot three-component reaction of dimedone/1,3-cyclohexanedione, aldehydes, and 5-aryl-1,3,4-thiadiazol-2-amines/3-(5-amino-1,3,4-thiadiazol-2-yl)-2H-chromen-2-one under solvent-free conditions. This catalyst was also successfully utilized for the synthesis of mono- and bis-thiadiazolo[2,3-b]quinazolin-6-ones from dialdehydes or bis-1,3,4-thiadiazol-2-amine. The simplicity of enforcement, short reaction time, avoidance of toxic organic solvents, scalability of the synthesis procedure, excellent atom economy, high reaction mass efficiency, and low E-factor are other outstanding advantages of this newly developed method. Furthermore, due to the convenient recovery and reuse of LA-DES, this protocol is economically justified and environmentally friendly.

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Tetrabutylammonium Hydrogen Sulfate mediated Three-Component Reaction for the Synthesis of Thiadiazolo [2,3-b] Quinazolin-6-(7H)-ones and Antioxidant Activity

Cited by 4 publications

References 10 publications

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions

Efficient synthesis of novel thiadiazolo[2,3-b]quinazolin-6-ones catalyzed by diphenhydramine hydrochloride-CoCl2⋅6H2O deep eutectic solvent

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