Thermal and microwave assisted synthesis of <i> N</i>-aroylamino acridinediones

Josephrajan, T.; Ramakrishnan, V. T.

doi:10.1139/v07-075

Cited by 11 publications

(7 citation statements)

References 11 publications

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“…As we know, tetraketones can be obtained from the Knoevenagel reaction followed by a Michael addition reaction of aromatic aldehydes with cyclic 1,3‐diketones in basic or acidic conditions. In addition, various fused heterocyclic compounds such as xanthenedione, thiaxanthenes, and acridinediones which are as an important part of many naturally and synthetically abundant biologically active compounds can be synthesized from tetraketones as significant precursors 18‐22 . Therefore, the designed organo‐nanocatalyst can be used as a nanoreactor in the synthesis of these biologically important compounds (tetraketones) with high yield.…”

Section: Resultsmentioning

confidence: 99%

KCC‐1‐nPr‐NH‐Argas an efficient organo‐nanocatalyst for the green synthesis of 1,8‐dioxo decahydroacridine derivatives

Hasannezhad

Shadjou

2022

J of Molecular Recognition

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In the present work, an innovative biocompatible heterogeneous organo-nanocatalyst is prepared based on the grafting of arginine amino acid on the channels and pores of dendritic fibrous nano silica. The designed organo-nanocatalyst (KCC-1-nPr-NH-Arg) was characterized by using field emission scanning electron microscopy, Fourier transform infrared spectroscopy, energy dispersive X-ray spectroscopy, map analysis, and adsorption/desorption instruments. The results of analysis show that the engineered catalyst has uniform fibrous spheres and dendritic structure with high surface area (104.9 m 2 /g) and great pore volume (0.83 cm 3 g À1 ). Because of exceptional dendritic structure of the prepared organo-nanocatalyst, the active sites are available and the difusion and adsorption capacity of the reagents and products increase in the pores and channels of the catalyst. Hence, KCC-1-nPr-NH-Arg was used as an capable heterogeneous basic nanocatalyst in the synthesis of 1,8-dioxo decahydroacridine derivatives from the one-pot four component reactions of aromatic aldehydes, dimedone, and ammonium acetate in solvent free conditions with shorter reaction times (13-35 minutes) and higher yields (94%-98%) in evaluation with other reported works. It is expected that the green organo-nanocatalyst can be used to synthesize other organic compounds.

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Section: Resultsmentioning

confidence: 99%

KCC‐1‐nPr‐NH‐Argas an efficient organo‐nanocatalyst for the green synthesis of 1,8‐dioxo decahydroacridine derivatives

Hasannezhad

Shadjou

2022

J of Molecular Recognition

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“…Tetraketone derivatives are considered not only as an important class of biologically active compounds but also as signicant precursors for the synthesis of various fused heterocyclic. 73 The structure of compound 21 was spectroscopically veried. In the IR spectrum, the carbonyl and the hydroxyl stretching frequencies were noticed at 1650 and 3345 cm À1 , respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of novel star-shaped molecules based on a 1,3,5-triazine core linked to different heterocyclic systems as novel hybrid molecules

et al. 2020

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“…Josephrajan and Ramakrishnan [183] demonstrated a comparative study of acridinediones synthesis under various reaction conditions using benzoic hydrazide and tetraketones as starting materials via MWI and conventional heating. The authors displayed three different conditions, in first case, reactants refluxed with P 2 O 5 and EtOH and in second case, MWI was applied.…”

Section: Synthesis Of Acridine‐18‐dione Derivativesmentioning

confidence: 99%

“…In 2005, Das and companions [182] reported Amberlyst-15 as a heterogeneous, economical and eco-friendly catalyst for the efficient synthesis of substituted acridinediones in CH 3 CN solvent to deliver high yields with simple recovery and high reusability [Scheme 32, Method 1]. Josephrajan and Ramakrishnan [183] demonstrated a comparative study of acridinediones synthesis under various reaction conditions using benzoic hydrazide and tetraketones as starting materials via MWI and conventional heating. The authors displayed three different conditions, in first case, Hereafter, Venkatesan et al [184] employed Proline as an easily available and non-toxic catalyst for the efficient synthesis of acridinediones in EtOH at 65°C and yielded good amount of products [Scheme 32, Method 2].…”

Section: Miscellaneous Protocolsmentioning

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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Thermal and microwave assisted synthesis of N-aroylamino acridinediones

Abstract: A series of N-aroylamino acridinediones (3a–3d and6a–6e) have been synthesized from tetraketones (1 and 4) and benzoic hydrazides (2a–2d and 5a–5e) under thermal and microwave irradiation conditions with solid supports.Key words: acridine, hydrazide, microwave irradiation.

Cited by 11 publications

References 11 publications

KCC‐1‐nPr‐NH‐Argas an efficient organo‐nanocatalyst for the green synthesis of 1,8‐dioxo decahydroacridine derivatives

KCC‐1‐nPr‐NH‐Argas an efficient organo‐nanocatalyst for the green synthesis of 1,8‐dioxo decahydroacridine derivatives

Synthesis of novel star-shaped molecules based on a 1,3,5-triazine core linked to different heterocyclic systems as novel hybrid molecules

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

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