A rapid and green method for expedient multicomponent synthesis of N-substituted decahydroacridine-1,8-diones as potential antimicrobial agents

Bhosle, Manisha R.; Nipte, Dhananjay; Gaikwad, Jivan; Shaikh, Mubarak H.; Bondle, Giribala M.; Sangshetti, Jaiprakash N.

doi:10.1007/s11164-018-3541-7

Cited by 20 publications

(37 citation statements)

References 47 publications

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“…Anilines containing electron‐ withdrawing and electron‐donating substituents at the para position were compatible with different alcohols and dimedone to form corresponding hexahydroacridine‐1,8‐diones. Our methodology offers a route to synthesize antimicrobial agent 5 k [13c] in 75% yield. When ( E )‐4‐styrylaniline was used, the desired 5 n was formed in moderate yield together with a small amount of C=C reduction product 5 n'(5 n : 5 n' 4 : 1) (Scheme 2, Entry 5 n and 5 n' ).…”

Section: Resultsmentioning

confidence: 99%

Multicomponent Dehydrogenative Synthesis of Acridine‐1,8‐diones Catalyzed by Ru‐doped Hydrotalcite

et al. 2021

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The usage of biomass‐derived chemicals to synthesize pharmaceutically important heterocyclic scaffold via acceptorless dehydrogenation is an emerging trend in chemistry. Herein, we describe the applicability of Ru‐doped hydrotalcite (Ru‐HT) in the dehydrogenative synthesis of structurally important acridine‐1,8‐dione derivatives. To highlight the practical utility, the gram‐scale synthesis of acridine‐1,8‐dione and the successful recyclability of the catalyst were shown.

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Section: Resultsmentioning

confidence: 99%

Multicomponent Dehydrogenative Synthesis of Acridine‐1,8‐diones Catalyzed by Ru‐doped Hydrotalcite

et al. 2021

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“…Bhosle and his companions [166] demonstrated ChCl:urea as an effective catalyst for the efficient synthesis of decahydroacridine‐1,8‐diones. The reaction of dimedone, substituted benzaldehydes and aniline in ChCl: urea at 80 °C furnished acridinediones in good yields with wide functionality.…”

Section: Synthesis Of Acridine‐18‐dione Derivativesmentioning

confidence: 99%

Acridine‐1,8‐diones: Synthesis and Biological Applications

Sahiba¹,

Sethiya²,

Soni³

et al. 2021

ChemistrySelect

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The unpretentious features of acridine‐1,8‐diones viz. presence of N‐heteroatom, electronic behavior, acridine ring skeleton and wide possibilities of diversified substitution, bichromophoric structure and interaction ability with various proteins, make them an interesting scaffold of heterocyclic, medicinal and industrial chemistry. A tremendous development in the field of acridinediones in terms of synthetic strategies, bioactivity, industrial and other applicability has been explored in past four decades. In this perspective, an overview has been given on the state‐of‐art discoveries for the synthesis and biological applications of acridine‐1,8‐diones from 1980 to 2020. The study highlighted the history, chemistry and properties of these derivatives and provided deep insights into the synthetic protocols using various catalysts and techniques like nano‐catalyst, ionic‐liquids, microwave, ultrasound etc. under varied conditions along with biological activity against many lethal diseases. Finally, the respective prospects and limitations to these systems have been addressed. Furthermore, attempts have been done to bring many outstanding researches together and express the significance of acridine‐1,8‐diones through several aspects. We hope that the article shall deliver an impetus to explore further the synthetic values and mechanistic puzzles of acridinedione moiety and to design more promising hybrid multi‐targeted drugs and other industrial composites for the goodness of humanity

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“…All catalytic reactions were carried out under an argon atmosphere using dry glassware and standard syringe/septa techniques. DRX-400 Varian and Bruker Avance III 600 and 400 spectrometers were used to record 1 H, 13 C{ 1 H} NMR, and 31 P NMR, respectively. Chemical shifts (δ) are reported in the ppm downfield from tetramethylsilane; spin−spin coupling constants (J) are expressed in Hz and other data are reported as follows: s = singlet, d = doublet, t = triplet, m = multiplet, q = quartet, and br s = broad singlet.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…To our delight, using a heteroaromatic alcohol such as 2-thiophene methanol as the substrate, compound 7m was isolated in 61% yield. Compound 7n has antimicrobial properties, 13 which can be easily prepared by this methodology with a good yield (66%). 2-Pyridine methanol and 2-aminopyridine also under the optimized reaction condition gave the desired product 7o and 7p in good to moderate yields.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis of 1,8-Dioxo-decahydroacridine Derivatives via Ru-Catalyzed Acceptorless Dehydrogenative Multicomponent Reaction

Biswas

Srimani

2021

J. Org. Chem.

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A Ru-catalyzed acceptorless dehydrogenative multicomponent reaction has been developed. This reaction offers a cost-effective and simple operational strategy to synthesize biologically active 1,8-dioxodecahydroacridine derivatives. The protocol provides a wide range of substrate scope and various functional groups are also well tolerated under the reaction condition. To shed light on the mechanistic and kinetic study, some controlled experiments and deuterium labeling experiments were executed. A time-dependent product distribution experiment is also presented and the reaction scale-up is performed to highlight the practical utility of this strategy.

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A rapid and green method for expedient multicomponent synthesis of N-substituted decahydroacridine-1,8-diones as potential antimicrobial agents

Cited by 20 publications

References 47 publications

Multicomponent Dehydrogenative Synthesis of Acridine‐1,8‐diones Catalyzed by Ru‐doped Hydrotalcite

Multicomponent Dehydrogenative Synthesis of Acridine‐1,8‐diones Catalyzed by Ru‐doped Hydrotalcite

Acridine‐1,8‐diones: Synthesis and Biological Applications

Synthesis of 1,8-Dioxo-decahydroacridine Derivatives via Ru-Catalyzed Acceptorless Dehydrogenative Multicomponent Reaction

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