Chromene-dihydropyrimidinone and xanthene-dihydropyrimidinone hybrids: design, synthesis, and antibacterial and antibiofilm activities

Santos, Sérgio Leandro dos; Rossato, Fernanda C. P.; Jardim, Natalia; Ávila, Daiana Silva; Ligabue-Braun, Rodrigo; Fontoura, Luiz Antonio Mazzini; Zimmer, Karine Rigon; Russowsky, Dennis

doi:10.1039/d2nj05211c

New J. Chem.

2023

DOI: 10.1039/d2nj05211c

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Chromene-dihydropyrimidinone and xanthene-dihydropyrimidinone hybrids: design, synthesis, and antibacterial and antibiofilm activities

Sérgio Leandro dos Santos

Fernanda C. P. Rossato

Natalia Jardim

et al.

Abstract: A series of eleven Chromene-Dihydropyrimidinone and eleven Xanthene-Dihydropyrimidinone hybrid compounds were easily synthesized through a sequential multicomponent reaction followed by the Copper-catalyzed Alkyne-Azide Cycloaddition reaction. The antibiofilm and antibacterial...

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Copper-carboxamide complex immobilized on nano NaY zeolite: an efficient catalyst for xanthenes synthesis

Younesi,

Asghari,

Firouzzadeh Pasha

et al. 2023

Res Chem Intermed

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Copper-carboxamide complex immobilized on nano NaY zeolite: an efficient catalyst for xanthenes synthesis

Younesi,

Asghari,

Firouzzadeh Pasha

et al. 2023

Res Chem Intermed

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Nonoxidovanadium(IV) Complex-Catalyzed Synthesis of 2-Amino-3-cyano-4H-pyrans/4H-chromenes, Biscoumarins, and Xanthenes under Green Conditions

Maurya,

Kumar

et al. 2024

J. Org. Chem.

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Reaction of [V IV O(acac) 2 ] (Hacac = acetylacetone) with a Mannich base, N,N,N′, N′-tetrakis(2-hydroxy-3,5-di-tert-butyl benzyl)-1,2-diaminoethane (H 4 L, I) in a 1:1 molar ratio in MeOH, leads to the formation of the nonoxidovanadium(IV) complex [V IV L] (1). Air stable complex 1 has been characterized using various spectroscopic techniques, DFT calculations, and single-crystal X-ray studies. 1 adopts distorted octahedral geometry where ligand coordinates through all coordination functionalities available. This complex has been used as a catalyst in the one-pot, three-component synthesis of 2-amino-3-cyano-4H-pyrans using 1,3-dicarbonyls (1,3-cyclohexanedione, dimedone, barbituric acid, and 4-hydroxycoumarin), malononitrile, and various substituted aromatic aldehydes in equimolar amounts employing ethanol as a green solvent. The catalytic reaction revealed that the multicomponent synthesis of 4H-pyrans and chromenes is greatly influenced by both types of 1,3-dicarbonyl compound employed and the nature of the substituent on the aromatic ring of the aldehyde. Synthesized catalyst has also been used in the synthesis of pharmacologically relevant oxygen-containing heterocycles, specifically, 1,8-dioxo-octahydro-1H-xanthenes and biscoumarins. The possible mechanism for the synthesized one-pot, multicomponent product has been proposed by isolating intermediate(s) generated during synthesis.

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Chromene-dihydropyrimidinone and xanthene-dihydropyrimidinone hybrids: design, synthesis, and antibacterial and antibiofilm activities

Abstract: A series of eleven Chromene-Dihydropyrimidinone and eleven Xanthene-Dihydropyrimidinone hybrid compounds were easily synthesized through a sequential multicomponent reaction followed by the Copper-catalyzed Alkyne-Azide Cycloaddition reaction. The antibiofilm and antibacterial...

Cited by 2 publications

References 65 publications

Copper-carboxamide complex immobilized on nano NaY zeolite: an efficient catalyst for xanthenes synthesis

Copper-carboxamide complex immobilized on nano NaY zeolite: an efficient catalyst for xanthenes synthesis

Nonoxidovanadium(IV) Complex-Catalyzed Synthesis of 2-Amino-3-cyano-4H-pyrans/4H-chromenes, Biscoumarins, and Xanthenes under Green Conditions

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