Ammonium Acetate: An Efficient Reagent for the One-pot Synthesis of 5-Aryl-7,8,13,14-tetrahydrodibenzo[a,i] phenanthridines, 2,4-Diaryl-6,7-benzo-3-azabicyclo[3.3.1]nonan-9-ones and α,α'-Bis(substituted benzylidene)cycloalkanones

doi:10.5012/bkcs.2009.30.11.2555

Bulletin of the Korean Chemical Society

2009

DOI: 10.5012/bkcs.2009.30.11.2555

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Ammonium Acetate: An Efficient Reagent for the One-pot Synthesis of 5-Aryl-7,8,13,14-tetrahydrodibenzo[a,i] phenanthridines, 2,4-Diaryl-6,7-benzo-3-azabicyclo[3.3.1]nonan-9-ones and α,α'-Bis(substituted benzylidene)cycloalkanones

Abstract: The condensation of cyclic ketone with aromatic aldehydes in the presence of ammonium acetate under ethanol media affords the corresponding 5-aryl-7,8,13,14-tetrahydrodibenzo[a,i]phenanthridine with excellent yield. This mild and efficient procedure with high yield is also applied to the synthesis of 2,4-diaryl-6,7-benzo-3-azabicyclo-[3.3.1]nonan-9-ones and α,α'-bis(substituted benzylidene)cycloalkanones.

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Cited by 19 publications

References 23 publications

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Selective Synthesis and Structural Confirmation of 1,3‐Oxazines and Schiff Bases with Controllable Substitution Patterns

et al. 2012

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Selective synthesis of 2,4‐diaryl‐2,3‐dihydro‐3H‐naphtho[1,2‐e]‐1,3‐oxazines and Schiff bases ((E)‐[1‐arylmethyl(benzylideneamino)]naphth‐2‐ols) that contain two identical or two different aryl substituents was achieved through one‐pot synthesis with ammonium acetate. From the proposed mechanism the dual role of ammonium acetate was identified. The synthesized products were characterized by 1H and 13C NMR spectroscopy, as well as FTIR and mass spectrometry. Crystal structures of the 1,3‐oxazines and Schiff base derivatives were examined. A notable feature is the conspicuous absence of strong donors (NH/OH) in any intermolecular hydrogen‐bonding scheme. Instead, packing is characterized by weak intermolecular CH⋅⋅⋅O, CH⋅⋅⋅π and CCl⋅⋅⋅π interactions, which lead to dimeric and zig‐zag one‐dimensional molecular patterns. The oxazine moiety of the tricyclic ring system predominantly adopts a half‐chair conformation. The present Mannich procedure is an environmentally benign and cost‐effective method for the preparation of industrially and pharmaceutically useful heterocyclic scaffolds.

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Selective Synthesis and Structural Confirmation of 1,3‐Oxazines and Schiff Bases with Controllable Substitution Patterns

et al. 2012

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Rational Synthesis of Tetrahydrodibenzophenanthridine and Phenanthroimidazole as Efficient Blue Emitters and their Applications

et al. 2020

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Ten luminophores based on tetrahydrodibenzophenanthridine (THDP) and phenanthroimidazole (PI) were designed, synthesized and characterized for their thermal, electrochemical, electro‐optical, charge‐transporting characteristics and electroluminescent properties. The blue luminophores exhibited high photoluminescence quantum yields of 66–93 % in toluene solutions and of 5–59 % in solid films. The highest values were observed for the derivative of THDP and PI containing methoxy group. The compounds showed close values of ionization potentials (5.74–6.11 eV) and electron affinities (2.71–3.06 eV). The selected compounds were tested in electroluminescent devices for the preparation of non‐doped light‐emitting layers. The best device fabricated using derivative of THDP and PI with methoxy groups showed blue electroluminescence with brightness of 10000 cd/m2 at high applied voltages. We performed DFT calculations and observed lowest singlet–triplet gap (ΔEST) values of 0.33 and 0.03 eV, oscillator strength (f) values of 0.034 and 0.008 for CN and NO2 derivatives. Interestingly, we also observed that compounds 3g and 3i showed HOMO and LUMO levels with similar energy gap (Eg) of 3.60 eV and deeper HOMO values of –5.30, –5.33 eV and LUMO values of –1.94, –2.77 eV.

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Phenanthridine‐Based Donor/Acceptor Fluorescent Dyes: Synthesis, Photophysical Properties and Fluorometric Sensing of Biogenic Primary Amines

et al. 2021

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Synthesis of two new and straight forward phenanthridine based fluorophores (PA1 and PA2) have been described. The molecular structure of PA1 and PA2 was confirmed by spectroscopic studies (1 H NMR, 13 C NMR and HRMS). The dyes are further characterized by comprehensive photophysical study, and their data are critically analyzed. The fluorescence properties of these DÀ A chromophores are highly influenced by the position of the hydroxyl substitution and the solvent polarity. These probes exhibited an arsenal of advantageous features such as higher Stokes shift values and appreciable photostability. Compounds PA1 and PA2 are found to be indicating fluorescent ratiometric detection towards primary amines (PAs) with high selectivity and sensitivity. With this background, sensing of PAs was extended to biogenic amines as they have primary amine functionality. As expected, these fluorophores have excellent detection ability towards neurotransmitters, such as dopamine (DA) and serotonin (SN) with a low limit of detection (LOD) such as 1.61 nM and 0.31 nM respectively. The sensing mechanism of the probe PA1 with PAs are based on the nucleophilic addition and confirmed through investigation by 1 H NMR titration, mass analysis and theoretical calculations. Moreover, sensor probe PA1 based test paper strip was developed, which could detect DA conveniently when visualized under 365 nm UV lamp.

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Ammonium Acetate: An Efficient Reagent for the One-pot Synthesis of 5-Aryl-7,8,13,14-tetrahydrodibenzo[a,i] phenanthridines, 2,4-Diaryl-6,7-benzo-3-azabicyclo[3.3.1]nonan-9-ones and α,α'-Bis(substituted benzylidene)cycloalkanones

Cited by 19 publications

References 23 publications

Selective Synthesis and Structural Confirmation of 1,3‐Oxazines and Schiff Bases with Controllable Substitution Patterns

Selective Synthesis and Structural Confirmation of 1,3‐Oxazines and Schiff Bases with Controllable Substitution Patterns

Rational Synthesis of Tetrahydrodibenzophenanthridine and Phenanthroimidazole as Efficient Blue Emitters and their Applications

Phenanthridine‐Based Donor/Acceptor Fluorescent Dyes: Synthesis, Photophysical Properties and Fluorometric Sensing of Biogenic Primary Amines

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