Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels−Alder Approach

Catozzi, Nicola; Edwards, Michael G.; Raw, Steven A.; Wasnaire, Pierre; Taylor, Richard J.K.

doi:10.1021/jo901761r

Cited by 51 publications

(13 citation statements)

References 93 publications

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“…Catozzi et al used a 2-step condensation/oxidative cyclocondensation methodology to overcome this. 40 Methyl thiol substituents on the core can be oxidised to the sulfone which can then become the site of an S N Ar attack for subsequent functionalisation. 41 Moody et al recently developed a copper-carbene route to synthesise 1,2,4-triazines.…”

Section: 24-triazinesmentioning

confidence: 99%

Tandem inverse-electron-demand hetero-/retro-Diels–Alder reactions for aromatic nitrogen heterocycle synthesis

2013

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The merged inverse-electron-demand hetero-Diels-Alder (ihDA)/retro-Diels-Alder (rDA) reaction sequence can be used to rapidly synthesise highly functionalised nitrogen heteroaromatics. The reaction offers many advantages: high atom economy, high levels of regioselectivity, it rarely requires a catalyst and, in some cases, can be performed in the absence of solvent. In this tutorial review we discuss the range of commonly used dienophiles and aza-dienes for this process whilst highlighting the reactivity trends, and illustrating their applications.

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Section: 24-triazinesmentioning

confidence: 99%

Tandem inverse-electron-demand hetero-/retro-Diels–Alder reactions for aromatic nitrogen heterocycle synthesis

2013

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“…In the present work, we synthesized a series of heterocyclic compounds derived from ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate together with their antitumor evaluations. Thus, the reaction of o-phenylenediamine (1) with diethylmalonate (2) in an oil bath at 120 o C gave ethyl 2-(1Hbenzo[d]imidazol-2-yl)acetate (3), its structure was based on analytical and spectral data. Compound 3 was used in many acyclic and heterocyclic reactions.…”

Section: Resultsmentioning

confidence: 99%

“…Their corresponding carbamate derivatives have been synthesized for their significant in vivo antifilarial activity [1]. Concerning the high affinity that they display towards a variety of enzymes and protein receptors, they could be considered as pivotal structures in drug design [2]. Optimization of benzimidazole-based structures has resulted in marketed drugs, e.g.…”

Section: Introductionmentioning

confidence: 99%

The uses of ethyl 2-(1H-benzo[D]imidazol-2-yl)acetate to synthesis pyrazole, thiophene, pyridine and coumarin derivatives with antitumor activities

Mohareb¹,

Gamaan²

2018

Bull. Chem. Soc. Eth.

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In the present work, the ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate (3) was subjected to a series of heterocyclization reactions through its reaction with different chemical reagents. The resulting molecules were thiophene, pyrazole, coumarin derivatives incorporated benzo[d]imidazole moiety. All the synthesized compounds were determined by elemental analysis, 1 H NMR, 13 C NMR, and MS. The antitumor evaluations of the newly synthesized products toward the three cancer cell lines MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), and SF-268 (CNS cancer) showed that compounds 5a, 9b, 9c, 17, 23b and 38 were of the highest potencies among the synthesized compounds.

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“…Triazines are analogues of benzene ring where the three carbons are replaced with nitrogens. The isomer, 1,2,4‐triazine, is the most reported isomer than the other two (1,2,3‐triazine and 1,3,5‐triazine) . 1,2,4‐Triazine and substituted triazines show antifungal , antiviral , anticancer , antibiotics , antiparasitic , anti‐HIV , antianxiety, and antiinflammatory activities, and its biochemical reactivity has been studied .…”

Section: Introductionmentioning

confidence: 99%

Substitution Kinetics of [Fe(PDT/PPDT)_n(phen)_m]²⁺(n≠m;n,m= 1,2) with 2,2′-Bipyridine, 1,10-Phenanthroline, and 2,2′,6,2″-Terpyridine

Bellam

Jaganyi

2017

Int. J. Chem. Kinet.

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The triazines 3-(2-pyridyl)-5,6-diphenyl-1,2,4-triazine (PDT), 3-(4-phenyl-2-pyridyl)-5,6-diphenyl-1,2,4-triazine (PPDT), and 1,10-phenanthroline (phen) were coordinated to the Fe 2+ ion to form Fe(PDT) 2 (phen) 2+ (1), Fe(PPDT) 2 (phen) 2+ (2), Fe(PDT)(phen) 2+ 2 , (3) and Fe(PPDT)(phen) 2+ 2 (4). The complexes were synthesized and characterized by mass spectroscopy and elemental analysis. The rate of substitution of these complexes by 2,2 -bipyridine (bpy), 1,10-phenanthroline (phen), and 2,2 ,6,2 -terpyridine (terpy) was studied in a sodium acetate-acetic acid buffers over the range 3.6-5.6 at 25, 35, and 45°C under pseudo-first-order conditions. The reactions are first order with respect to the concentration of the complexes. The reaction rates increase with increasing [bpy/phen/terpy] and pH, whereas ionic strength has no influence on the rate of reaction. Plots of k obs versus [bpy/phen/terpy] and 1/[H + ] are linear with positive slopes and significant y-intercepts. This indicates that the reactions proceed by both dissociative as well as associative pathways for which the associative pathway predominates the substitution kinetics. Observed temperature-depended rate constants at the three temperatures at which substitution reactions were studied together with the protonation constants of the substituting ligands (phen, bpy, terpy) were used to evaluate the specific rate constants (k 1 and k 2 ) and thermodynamic parameters (E a , H # , S # , and G # ). The reactivity order of the four complexes depends on the phenyl groups present on the triazine (PDT/PPDT)Correspondence to: R. Bellam; e-mail: rajeshchowdarybellam@ gmail.com.Supporting Information is available in the online issue at www.wileyonlinelibrary.com.C 2017 Wiley Periodicals, Inc. SUBSTITUTION KINETICS OF [Femolecule. The π -electrons on phenyl rings stabilizes the charge on the metal center by inductive donation of electrons toward the metal center resulting in a decrease in reactivity of the complex, and the order is 1 < 2 < 3 < 4. The rate of substitution is also influenced by the basicity of the incoming ligand (bpy/phen/terpy), and it decreased in the order: phen > terpy > bpy. Higher rate constants, low E a values , and more negative entropy of activation (− S # ) values were observed for the associative path, revealing that substitution reactions at the octahedral iron(II) complexes by bpy, phen, and terpy occur predominantly by the associative mechanism. Density functional theory calculations support the interpretations.

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Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels−Alder Approach

Cited by 51 publications

References 93 publications

Tandem inverse-electron-demand hetero-/retro-Diels–Alder reactions for aromatic nitrogen heterocycle synthesis

Tandem inverse-electron-demand hetero-/retro-Diels–Alder reactions for aromatic nitrogen heterocycle synthesis

The uses of ethyl 2-(1H-benzo[D]imidazol-2-yl)acetate to synthesis pyrazole, thiophene, pyridine and coumarin derivatives with antitumor activities

Substitution Kinetics of [Fe(PDT/PPDT)_n(phen)_m]²⁺(n≠m;n,m= 1,2) with 2,2′-Bipyridine, 1,10-Phenanthroline, and 2,2′,6,2″-Terpyridine

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Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels−Alder Approach

Cited by 51 publications

References 93 publications

Tandem inverse-electron-demand hetero-/retro-Diels–Alder reactions for aromatic nitrogen heterocycle synthesis

Tandem inverse-electron-demand hetero-/retro-Diels–Alder reactions for aromatic nitrogen heterocycle synthesis

The uses of ethyl 2-(1H-benzo[D]imidazol-2-yl)acetate to synthesis pyrazole, thiophene, pyridine and coumarin derivatives with antitumor activities

Substitution Kinetics of [Fe(PDT/PPDT)n(phen)m]2+(n≠m;n,m= 1,2) with 2,2′-Bipyridine, 1,10-Phenanthroline, and 2,2′,6,2″-Terpyridine

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Substitution Kinetics of [Fe(PDT/PPDT)_n(phen)_m]²⁺(n≠m;n,m= 1,2) with 2,2′-Bipyridine, 1,10-Phenanthroline, and 2,2′,6,2″-Terpyridine