A simple and environmentally benign synthesis of novel spiro[indoline-3,5′-pyrano[2,3-d]pyrimidine] derivatives in water

Ghadiri, Sakineh; Bayat, Mohammad; Hosseini, Fahimeh Sadat

doi:10.1007/s00706-019-2356-6

Cited by 14 publications

(11 citation statements)

References 27 publications

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“…Ghadiri and co-workers 191 developed a greener synthetic route to afford a novel analogue of spiropyranopyrimidine, 156 , by using a three-component equimolar reaction of 24 with 11 / 11a , and N -alkyl-1-(methylthio)-2-nitroethenamine 155 was derived via the reaction of discrete amine 154 with nitroketene dithioacetal 153 in green solvent water (10 mL) under reflux for 7–10 h ( Scheme 105 ). Reactions showed in Scheme 105 took highest reaction time than the other reaction in this section of the present review.…”

Section: Synthesis Of 5-aryl-substituted Pyrano[23- D ...mentioning

confidence: 99%

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

2023

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The pyranopyrimidine core is a key precursor for medicinal and pharmaceutical industries due to its broader synthetic applications as well as its bioavailability. Among its four possible isomers, we found that 5H-pyrano[2,3-d]pyrimidine scaffolds have a wide range of applicability, and in recent years, they have been intensively investigated, but the development of the main core is found to be more challenging due to its structural existence. In this review article, we cover all of the synthetic pathways that are employed for the development of substituted 4-aryl-octahydropyrano/hexahydrofuro[2,3-d]pyrimidin-2-one (thiones) and 5-aryl-substituted pyrano[2,3-d]pyrimidindione (2-thiones) derivatives through a one-pot multicomponent reaction using diversified hybrid catalysts such as organocatalysts, metal catalysts, ionic liquid catalysts, nanocatalysts, green solvents, catalyst-/solvent-free conditions, and miscellaneous catalysts as well as the mechanism and recyclability of the catalysts. This review mainly focuses on the application of hybrid catalysts (from 1992 to 2022) for the synthesis of 5H-pyrano[2,3-d]pyrimidine scaffolds. This review will definitely attract the world’s leading researchers to utilize broader catalytic applications for the development of lead molecules.

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Section: Synthesis Of 5-aryl-substituted Pyrano[23- D ...mentioning

confidence: 99%

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

2023

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“…The structures of some important and biologically active compounds containing spirocyclic rings are shown in Figure. 1 [6–26] …”

Section: Introductionmentioning

confidence: 99%

Greener Synthesis, Molecular Docking and Anticancer Studies of A New Series of 6‐Hydroxy‐5‐(3‐(3‐hydroxy‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)‐2‐oxoindolin‐3‐yl) pyrimidine‐2,4(1H,3H)‐diones

Tamilselvi,

Subramani Maheswari,

Kavishree

et al. 2024

ChemistrySelect

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Greener solvent mediated simple and efficient synthesis of 6‐hydroxy‐5‐(3‐(3‐hydroxy‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)‐2‐oxoindolin‐3‐yl)pyrimidine‐2,4(1H,3H)‐diones has been achieved through the one‐pot multicomponent condensation reaction between 2‐hydroxy‐1,4‐naphthoquinone, substituted isatin and barbituric acid/thiobarbituric acid/1,3‐dimethylbarbituric acid using ethanol‐water as a solvent without any catalyst at room temperature has been described. Molecular docking studies have been performed with Akt kinase enzyme protein which helped to rationalize the binding energy of all the synthesized compounds. The docking of compound 4d, with human Akt kinase enzyme showed a good binding interaction with lowest binding energy. Based on the results from the molecular docking studies, the compound 4d was further studied for its in‐vitro anticancer activity against human breast cancer cells (MCF‐7) and human normal breast cells (HBL 100) by MTT assay which also proved the potential anticancer activity of 4d.

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“…These structures are used as biological agents and pharmaceutical applications [24,25]. They include anti‐helminthic [26], antibacterial, fungicidal [27], anticancer [28,29] antitumor, antiallergic [30], antimicrobial, antiviral [31–33] spasmolytic [34,35], anti‐HIV [36], and anti‐depressant [37] properties. Some naturally occurring chromenes that possess biological activities [38] are shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

“…Functionalized N,S ‐acetals have been utilized in many heterocyclic preparations and attracted much attention from many chemists in recent years [39–44]. The unique arrangement of nitroketene N,S ‐acetals reactive sites toward attack by electrophiles and nucleophiles (Figure 2), make them extremely workable and convenient in some strategies such as Michael addition, annulation, cyclization, and MCRs [39].…”

Section: Introductionmentioning

confidence: 99%

One‐pot synthesis of new functionalized 4H‐chromen‐4‐ylidene derivatives

Saeni

Bayat

Hosseini

2021

Journal of Heterocyclic Chem

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A simple synthesis of new series of functionalized chromene derivatives through an efficient, one‐pot, multicomponent reaction of nitroketene N,S‐acetals, salicylaldehydes, and cyanoacetohydrazide in ethanol at ambient temperature in good to high yields is reported. This novel efficient method has the advantages of mild reaction conditions, absence of catalyst, simple work‐up, and the non‐chromatographic purification of products.

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A simple and environmentally benign synthesis of novel spiro[indoline-3,5′-pyrano[2,3-d]pyrimidine] derivatives in water

Cited by 14 publications

References 27 publications

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

Greener Synthesis, Molecular Docking and Anticancer Studies of A New Series of 6‐Hydroxy‐5‐(3‐(3‐hydroxy‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)‐2‐oxoindolin‐3‐yl) pyrimidine‐2,4(1H,3H)‐diones

One‐pot synthesis of new functionalized 4H‐chromen‐4‐ylidene derivatives

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