NaN<sub>3</sub>Catalyzed Highly Convenient Access to Functionalized 4<i>H</i>-chromenes: A Green One-pot Approach for Diversity Amplification

Ramesh, Rathinam; Maheswari, Subramani; Małecki, Jan Grzegorz; Lalitha, Appaswami

doi:10.1080/10406638.2018.1564678

Cited by 19 publications

(10 citation statements)

References 49 publications

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“…2‐Aminopyridine (2‐AP) also exhibited good catalytic activity in this 3‐MCR, although the reaction scope reported by Lalitha and co‐workers was limited (only 2 examples reported) (Scheme 59B) [119] . The same research group prepared one spirooxindole applying sodium azide as catalyst (the scope of the reaction was directed to aldehydes, rather than isatins) (Scheme 59C) [120] . Nurjamal and Brahmachari used sodium formate to prepare a small library of spiro[indoline‐3,5’‐pyrido[2,3‐ d ]pyrimidine] derivatives (7 examples) (Scheme 59D).…”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

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Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

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Section: Spirooxindole Derivativesmentioning

confidence: 99%

“…L ‐proline and melamine [63] cinchona alkaloid‐thiourea [64] cinchona alkaloids [65] THAM [93] quinolinic acid [118] 2‐aminopyridine [119] NaN 3 [120] sodium formate [121] CSA [130] BINOL‐derivative phosphoric acid [153] …”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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“…4H-ch are generally prepared by a one-pot synthesis using different 2-benzylidene malononitriles and substituted resorcinols in the presence of methanol and calcium hydroxide at room temperature (Kolla and Lee, 2011 ). In addition, the reported methods consist of the condensation of resorcinol, aryl aldehydes, and malononitrile in the presence of diethylamine under reflux using ethanol as a solvent or 2-aminopyridine as an efficient organo-base-catalyst (Ramesh et al, 2019 ). Also, 2H-ch analogs are synthesized by the involving Witting-Horner-Emmons and Suzuki-Miyaura cross-coupling pallado-catalyzed reactions (Kaoukabi et al, 2019 ).…”

Section: Introductionmentioning

confidence: 99%

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

2020

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2H/4H-chromene (2H/4H-ch) is an important class of heterocyclic compounds with versatile biological profiles, a simple structure, and mild adverse effects. Researchers discovered several routes for the synthesis of a variety of 2H/4H-ch analogs that exhibited unusual activities by multiple mechanisms. The direct assessment of activities with the parent 2H/4H-ch derivative enables an orderly analysis of the structure-activity relationship (SAR) among the series. Additionally, 2H/4H-ch have numerous exciting biological activities, such as anticancer, anticonvulsant, antimicrobial, anticholinesterase, antituberculosis, and antidiabetic activities. This review is consequently an endeavor to highlight the diverse synthetic strategies, synthetic mechanism, various biological profiles, and SARs regarding the bioactive heterocycle, 2H/4H-ch. The presented scaffold work compiled in this article will be helpful to the scientific community for designing and developing potent leads of 2H/4H-ch analogs for their promising biological activities.

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“…Given this, a large number of catalysts were introduced for the three‐component synthesis of tetrahydrobenzo[ b ]pyran and pyrano[2,3‐ d ]‐pyrimidinone/thiones under multifarious catalytic circumstances. [ 9 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 ] There are numerous catalysts derived from fruit extracts, and agro‐wastes have been utilized to synthesize various heterocycles. [ 35 , 36 , 37 , 38 , 39 ]…”

Section: Introductionmentioning

confidence: 99%

“…[8] The diminution of by-products by means of straightforward synthesis of complex molecules exclusive of the segregation of the intermediates makes MCRs an imperative tactic in organic synthesis over multistep reactions also owing to the constitution of numerous new bonds in a single process. [9] Intellectual as well as industrial chemists are constantly striving to figure out the adequate sustainable replacements for expensive, toxic, hazardous, and environmental damaging catalysts. Thus, there is an invariable necessitate for most advantageous, fruitful, and eco-friendly catalysts.…”

Section: Introductionmentioning

confidence: 99%

WELPSA: A natural catalyst of alkali and alkaline earth metals for the facile synthesis of tetrahydrobenzo[b]pyrans and pyrano[2,3‐d]pyrimidinones as inhibitors of SARS‐CoV‐2

Nesaragi

Kamble

Hoolageri

et al. 2021

Applied Organom Chemis

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Since 2019, the infection of SARS‐CoV‐2 has been spreading worldwide and caused potentially lethal health problems. In view of this, the present study explores the most commodious and environmentally benign synthetic protocol for the synthesis of tetrahydrobenzo[ b ]pyran and pyrano[2,3‐ d ]pyrimidinones as SARS‐CoV‐2 inhibitors via three‐component cycloaddition of aromatic aldehyde, malononitrile, and dimedone/barbituric acid in water. Lemon peel from juice factory waste, namely, lemon ( Citrus limon ), sweet lemon ( C. limetta ), and Kaffir lime or Citron ( C. hystrix ), effectually utilized to obtain WELPSA, WESLPSA, and WEKLPSA, respectively, for the synthesis of title compounds. The catalyst was characterized by scanning electron microscope (SEM) and energy‐dispersive x‐ray spectroscopy (EDX). The concentration of sodium, potassium, calcium, and magnesium in the catalyst (WELPSA) was determined using atomic absorption spectrometry (AAS). The current approach manifests numerous notable advantages that include ease of preparation, handling and benignity of the catalyst, low cost, green reaction conditions, facile workup, excellent yields (93%–97%) with extreme purity, and recyclability of the catalyst. Compounds were docked on the crystal structure of SARS‐CoV‐2 (PDB: 6M3M). The consensus score obtained in the range 2.47–4.63 suggests that docking study was optimistic indicating the summary of all forces of interaction between ligands and the protein.

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NaN₃Catalyzed Highly Convenient Access to Functionalized 4H-chromenes: A Green One-pot Approach for Diversity Amplification

Cited by 19 publications

References 49 publications

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

WELPSA: A natural catalyst of alkali and alkaline earth metals for the facile synthesis of tetrahydrobenzo[b]pyrans and pyrano[2,3‐d]pyrimidinones as inhibitors of SARS‐CoV‐2

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NaN3Catalyzed Highly Convenient Access to Functionalized 4H-chromenes: A Green One-pot Approach for Diversity Amplification

Cited by 19 publications

References 49 publications

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

WELPSA: A natural catalyst of alkali and alkaline earth metals for the facile synthesis of tetrahydrobenzo[b]pyrans and pyrano[2,3‐d]pyrimidinones as inhibitors of SARS‐CoV‐2

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NaN₃Catalyzed Highly Convenient Access to Functionalized 4H-chromenes: A Green One-pot Approach for Diversity Amplification