An efficient KHSO<sub>4</sub> catalyzed synthesis of xanthenes

Reddy, N. Bakthavatchala; Rao, K. Ramakrishna; Sundar, Chereddy Syama; Nayak, Sandip K.; Reddy, C. Suresh

doi:10.1515/hc-2011-0057

2012

DOI: 10.1515/hc-2011-0057

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An efficient KHSO₄ catalyzed synthesis of xanthenes

N. Bakthavatchala Reddy

K. Ramakrishna Rao

Chereddy Syama Sundar

et al.

Abstract: KHSO 4 is an effi cient catalyst for the condensation of β -naphthol, aromatic aldehydes, and 5,5-dimethyl-1,3-cyclohexanedione at 100 ° C to afford 9,9-dimethyl-12-phenyl-8, 10,11,12-tetrahydro-9 H -benzo[ a ]xanthen-11-one derivatives in 80 -95 % yields.

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Cited by 4 publications

References 19 publications

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Synthesis and Bioassay of Dihydropyrano[3,2‐b]chromenediones

Chereddy

Reddy

Balam

et al. 2015

Journal of Heterocyclic Chem

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Ytterbium perfluorooctanoate [Yb(PFO)3] is found to be an efficient catalyst for the microwave‐irradiated synthesis of dihydropyrano[3,2‐b]chromenediones by the one‐pot condensation of kojic acid, aldehydes, and 1,3‐dicarbonyl compound under solvent‐free conditions. This approach offers many advantages, such as excellent product yields in short reaction time, solvent‐free conditions, easy isolation of products, low catalyst loading, reusability of the catalyst, and the absence of volatile and hazardous emissions. The preliminary antimicrobial results of in vitro biological studies showed that most of the newly synthesized compounds display a moderate inhibitory activity against bacteria and fungi. The complete characterization of synthesized compounds and bioassay results are provided.

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Synthesis and Bioassay of Dihydropyrano[3,2‐b]chromenediones

Chereddy

Reddy

Balam

et al. 2015

Journal of Heterocyclic Chem

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A meglumine catalyst–based synthesis, molecular docking, and antioxidant studies of dihydropyrano[3, 2‐b]chromenedione derivatives

Sravya

Suresh

Zyryanov

et al. 2019

Journal of Heterocyclic Chem

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A simple method was employed for the synthesis of dihydropyrano [3, 2-b] chromenedione derivatives (4a-o) in high yields by condensation of 5, 5dimethylcyclohexane-1, 3-dione(1), different aromatic aldehydes (2a-o), and 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one(3), using meglumine as a stable and reusable catalyst. Meglumine, an amino sugar, was employed as an environmentally benign catalyst, due to its splendid properties such as being inexpensive, recyclable, and biodegradable. The accomplished protocol employs low catalyst loading and easy work-up for the synthesis of 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one derivatives. A great asset is that without any significant loss, the catalyst could be recovered and reused for extended synthetic steps. This offer huge advantage to overcome recyclability issues. Our synthesized compounds were analyzed by IR, 1 H, 13 C NMR, mass spectra and evaluated for their antioxidant properties by 1, 1-diphenyl-2-picryl hydrazyl radical (DPPH), hydrogen peroxide(H 2 O 2 ), and nitric oxide (NO) scavenging methods. The correlation in exhibition of antioxidant activity was effective at all doses. The binding interactions and molecular docking studies for entitled compounds were studied against 3MNG protein; 4k exhibited marked binding affinity with excellent docking score of −7.6 Kcal/mol and emerged as a lead compound.

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Eco-friendly synthesis of tetrahydrobenzo[c]xanthenes catalyzed by functional ionic liquid in water

Yang

Tao³

et al. 2013

Monatsh Chem

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An efficient KHSO₄ catalyzed synthesis of xanthenes

Abstract: KHSO 4 is an effi cient catalyst for the condensation of β -naphthol, aromatic aldehydes, and 5,5-dimethyl-1,3-cyclohexanedione at 100 ° C to afford 9,9-dimethyl-12-phenyl-8, 10,11,12-tetrahydro-9 H -benzo[ a ]xanthen-11-one derivatives in 80 -95 % yields.

Cited by 4 publications

References 19 publications

Synthesis and Bioassay of Dihydropyrano[3,2‐b]chromenediones

Synthesis and Bioassay of Dihydropyrano[3,2‐b]chromenediones

A meglumine catalyst–based synthesis, molecular docking, and antioxidant studies of dihydropyrano[3, 2‐b]chromenedione derivatives

Eco-friendly synthesis of tetrahydrobenzo[c]xanthenes catalyzed by functional ionic liquid in water

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An efficient KHSO4 catalyzed synthesis of xanthenes

Abstract: KHSO 4 is an effi cient catalyst for the condensation of β -naphthol, aromatic aldehydes, and 5,5-dimethyl-1,3-cyclohexanedione at 100 ° C to afford 9,9-dimethyl-12-phenyl-8, 10,11,12-tetrahydro-9 H -benzo[ a ]xanthen-11-one derivatives in 80 -95 % yields.

Cited by 4 publications

References 19 publications

Synthesis and Bioassay of Dihydropyrano[3,2‐b]chromenediones

Synthesis and Bioassay of Dihydropyrano[3,2‐b]chromenediones

A meglumine catalyst–based synthesis, molecular docking, and antioxidant studies of dihydropyrano[3, 2‐b]chromenedione derivatives

Eco-friendly synthesis of tetrahydrobenzo[c]xanthenes catalyzed by functional ionic liquid in water

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An efficient KHSO₄ catalyzed synthesis of xanthenes