Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2<i>H</i>)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition

Boraei, Ahmed T. A.; Ghabbour, Hazem A.; Sarhan, Ahmed A. M.; Barakat, Assem

doi:10.1021/acsomega.0c00045

Cited by 9 publications

(7 citation statements)

References 38 publications

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“…Previously, we reported a simple efficient method for the synthesis of 4-methyl/phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one 4 and 7 from ninhydrin through a reaction first with ethyl acetoacetate or ethyl benzoylacetate and then a reaction of the resultant esters with hydrazine hydrate [32,33] (Scheme 1). Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis of 4-Methyl/phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-ones 4 and 7 from nihydrin is described in [32,33].…”

Section: Methodsmentioning

confidence: 99%

“…Additionally, this process can be used to create benzo[c] [2,6]naphthyridines and chromeno [4,3-c]pyridines in mild yields [30]. Recent research by Boraei et al has shown a simple and sustainable approach to the creation of tatraazafluoranthenones by using β-ketoesters such as ethyl acetoacetate and ethyl benzoylacetate with ninhydrin in green solvents such as water [31][32][33].…”

Section: Introductionmentioning

confidence: 99%

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4-Methyl/Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-ones Synthesis: Mechanistic Pathway Study and Single-Crystal X-ray Analysis of the Intermediates

Sarhan,

Haukka,

Barakat

et al. 2023

Crystals

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The synthesis of 4-methyl/phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one 4 and 7 has been reported with ninhydrin via a reaction first with ethyl acetoacetate or ethyl benzoylacetate and then a reaction of the resultant esters with hydrazine hydrate. The mechanism of hydrazinolysis and cyclization to obtain tetraazafluoranthen-3(2H)-ones is ambiguous, and the previously proposed mechanism was not based on facts because the actual intermediates were not isolated. Herein, the important intermediates involved in the hydrazinolysis–cyclization mechanistic pathway were isolated and characterized using NMR and X-ray single-crystal analysis. The intermediates demonstrate that the reaction carried out via two hydrazinolysis–cyclization reactions, the first of which includes the condensation of one hydrazine molecule with two ketone groups and the second of which includes the reaction of another hydrazine molecule with the ester and then condensation with the other ketone group. The stability of hydrazide 11 enabled the hydrazine to reduce the carbonyl of the ketone group to form 12 via a Wolff–Kishner-like reduction. The structure of the three intermediates was confirmed using X-ray crystallographic analysis. It was found that the three fused ring systems deviated from planarity to different extents, with their deviation from being coplanar reaching up to 5.3°. The possible non-covalent interactions which control the molecular packing of these intermediates were elucidated with the aid of Hirshfeld analysis.

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Section: Resultsmentioning

confidence: 99%

“…The synthesis of 4-Methyl/phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-ones 4 and 7 from nihydrin is described in [32,33].…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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4-Methyl/Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-ones Synthesis: Mechanistic Pathway Study and Single-Crystal X-ray Analysis of the Intermediates

Sarhan,

Haukka,

Barakat

et al. 2023

Crystals

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“…Diels–Alder reaction and transition metal-catalyzed reactions are the most commonly used methods for their synthesis. 36–38…”

Section: Introductionmentioning

confidence: 99%

Fluoranthene dyes for the detection of water content in methanol

Liu

Zhou

et al. 2022

RSC Adv.

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“…Very recently, Boraei group explored the unique reactivity of ninhydrin‐ethylacetoacetate (EAA) adduct 91 for the construction of different heterocyclic scaffolds . Reaction of adduct 91 with hydrazine hydrate in water afforded tetraazafluoranthen‐3‐(2H)‐one 93 in good yield (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Ninhydrin Adducts as Valid Synthon in Organic Synthesis: A Review

Das¹,

Dutta

2020

ChemistrySelect

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Ninhydrin (1,2,3‐indanetrione hydrate) is a powerful electrophile having enormousapplications in organic and bio‐organic sciences. In the last few years, reactivity of various ninhydrin adducts have been exploited extensively for the development of diverse organic scaffolds. The present review focuses on the applications of readily accessible ninhydrin adducts as building block towards the synthesis of a variety of compounds including N‐inserted compounds, spiro‐heterocycles, medium ring compounds, polycyclic molecules, propellanes, cycloadducts, allylic anions, axially chiral molecules etc. Interestingly, some of the compounds have profound biological activities and a few display important photophysical properties. Most of the reactions described here are simple and carried out with easily available starting materials under green conditions.

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Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition

Cited by 9 publications

References 38 publications

4-Methyl/Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-ones Synthesis: Mechanistic Pathway Study and Single-Crystal X-ray Analysis of the Intermediates

4-Methyl/Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-ones Synthesis: Mechanistic Pathway Study and Single-Crystal X-ray Analysis of the Intermediates

Fluoranthene dyes for the detection of water content in methanol

Ninhydrin Adducts as Valid Synthon in Organic Synthesis: A Review

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