Montmorillonite clay Cu(II) catalyzed domino one-pot multicomponent synthesis of 3,5-disubstituted isoxazoles

Bharate, Sandip B.; Padala, Anil K.; Dar, Bashir Ahmad; Yadav, Rammohan R.; Singh, Baldev; Vishwakarma, Ram A.

doi:10.1016/j.tetlet.2013.04.102

Cited by 38 publications

(14 citation statements)

References 30 publications

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“…Compounds were synthesized through a [3 + 2] cycloaddition reaction between terminal acetylenes with 5‐nitrofuraldehyde chloro‐oxime. The 5‐nitrofuraldehyde chloro‐oxime 17 was synthesized from 5‐nitrofuraldehyde 15 in two steps (Scheme ) …”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5‐disubstituted isoxazole compounds based on 5‐nitrofuran scaffolds

Trefzger

Barbosa

Scapolatempo

et al. 2019

Archiv der Pharmazie

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Nineteen 3,5-disubstituted-isoxazole analogs were synthesized based on nitrofuran scaffolds, by a [3 + 2] cycloaddition reaction between terminal acetylenes and 5-nitrofuran chloro-oxime. The compounds were obtained in moderate to very good yields (45-91%). The antileishmanial activity was assayed against the promastigote and amastigote forms of Leishmania (Leishmania) amazonensis. Alkylchlorinated compounds 14p-r were active on both the promastigote and amastigote forms, with emphasis on compound 14p, which showed strong activity against the amastigote form (IC 50 = 0.6 μM and selectivity index [SI] = 5.2). In the alkyl series, compound 14o stands out with an IC 50 = 8.5 μM and SI = 8.0 on the amastigote form. In the aromatic series, the most active compounds were those containing electron-donor groups, such as trimethoxy isoxazole 14g (IC 50 = 1.2 μM and SI = 20.2); compound 14h, with IC 50 = 7.0 μM and SI = 6.1; and compound 14j containing the 4-SCH 3 group, with IC 50 = 5.7 μM and SI = 10.2. In addition, the antifungal activity of 19 nitrofuran isoxazoles was evaluated against five strains of Candida (C. albicans, C. parapsilosis, C. krusei, C. tropicalis, and C. glabrata). Eleven isoxazole derivatives were active against C. parapsilosis, and compound 14o was found to be the most active (minimal inhibitory concentration [MIC] = 3.4 μM) for this strain. Compound 14p was active against all the strains tested, with an MIC = 17.5 μM for C. glabrata, lower than that of the fluconazole used as the reference drug. K E Y W O R D S5-nitrofuran scaffolds, antifungal activity, antileishmanial activity, drug design, isoxazole core *Ozildéia S. Trefzger, Natália V. Barbosa, and Renata L. Scapolatempo contributed equally to this work.

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Section: Resultsmentioning

confidence: 99%

Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5‐disubstituted isoxazole compounds based on 5‐nitrofuran scaffolds

Trefzger

Barbosa

Scapolatempo

et al. 2019

Archiv der Pharmazie

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“…Adicionalmente, possuem excelentes propriedades de adsorção, grande potencial para permuta iônica e elevada área de superfície específica, apresentam disponibilidade comercial, baixo custo, fácil manipulação, não corrosividade e reutilizável [3,5]. Em função desses atributos, o emprego das montmorilonitas como catalisadores ou promotores de reações orgânicas tem ganhado notoriedade no meio acadêmico durante os últimos anos [13][14][15][16][17]. O interesse dos químicos é traduzido pelos inúmeros relatos de sua utilização em reações orgânicas importantes como: alquilação [18] e acilação [19] de Friedel Crafts; nitração [20]; halogenação de compostos aromáticos [21]; reações de Diels-Alder [22]; reações de Baylis-Hillman [23]; rearranjo de Ferrier [24]; reações de Baeyer-Villiger [25]; adição de Michael [26]; propagilação [27]; dentre outras [13][14][15][16][17].…”

Section: Introductionunclassified

Uma acetilação eficiente e econômica do 1,2:3,4-di-O-isopropilideno-α-D-galactopiranose utilizando anidrido acético ativado in situ pela argila montmorilonita K10

Santos

Filho

et al. 2018

Cerâmica

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Resumo A síntese do 6-acetil 1,2:3,4-di-O-isopropilideno-α-D-galactopiranose a partir da reação de acetilação do 1,2:3,4-di-O-isopropilideno-α-D-galactopiranose utilizando a argila montmorilonita K10 como promotor é descrita. O protocolo é rápido, eficiente, econômico, livre de solvente e quimiosseletivo. O produto foi obtido em excelente rendimento (95%), curto tempo reacional (7,5 min), em temperatura ambiente e sem a necessidade de purificação adicional. Adicionalmente, essa argila manteve sua atividade catalítica por três ciclos reacionais sem diminuição de eficiência.

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“…Heterocyclic compounds play a significant role in drug discovery as they possess diverse activities such as antifungal, anti-inflammatory, anti-HIV, antimicrobial and anti-psoriatic etc 1 . Studies on multicomponent reactions (MCRs) are gaining interest due to the advantages such as mild reaction conditions and shorter reaction steps involved in the synthesis of complex molecules [2][3][4][5][6] . Green chemistry involves atom efficiency, reduced use of solvents, reusable solvents, reagents etc., 7,8 .…”

Section: Introductionmentioning

confidence: 99%

One Pot Multicomponent Synthesis of Novel Thiazolopyrimidines

2018

Chem Sci Trans

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A novel, solvent-free, simple, eco-friendly and one-pot multicomponent synthesis of various thiazolopyrimidines is studied. Conventional heating the mixture of amine, aldehyde and βketoester or 1,3-diketone under solvent free conditions afforded the thiazolopyrimidines compound in good to excellent yields. Further, a boron trifluoride mediated intermolecular cyclization to provide a novel tetra cyclic system is also reported. 1 H NMR, 13 C NMR, IR and Mass spectroscopy and single crystal analysis were used for identification of these compounds.

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Montmorillonite clay Cu(II) catalyzed domino one-pot multicomponent synthesis of 3,5-disubstituted isoxazoles

Cited by 38 publications

References 30 publications

Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5‐disubstituted isoxazole compounds based on 5‐nitrofuran scaffolds

Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5‐disubstituted isoxazole compounds based on 5‐nitrofuran scaffolds

Uma acetilação eficiente e econômica do 1,2:3,4-di-O-isopropilideno-α-D-galactopiranose utilizando anidrido acético ativado in situ pela argila montmorilonita K10

One Pot Multicomponent Synthesis of Novel Thiazolopyrimidines

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