Zuhal Turgut

Synthesis of new 1,3-disubstituted-2,3-dihydro-1H-naphth[1,2e][1,3]oxazines.

1,3-Disubstituted-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines were prepared through the ring-closure reactions of the aminobenzylnaphthols with substituted aryl- and heteroarylaldehydes.

Synthesis of New Pyrazolothiazole Derivatives from 4-Thiazolidinones

The synthesis of new 2,3,5,6-aryl substituted tetrahydro-2H-pyrazolo[3,4-d]- thiazoles 4a-j as potential biologically active compounds by the cyclocondensation of phenyl hydrazine with new 5-arylidene derivatives 2a-j of 2,3-disubstituted-1,3- thiazolidin-4-ones 1a-e is reported.

Allylation and Heterocycloaddition Reactions of Aldimines: Furan- and Quinolinecarboxaldehydes

Summary. New derivatives of α-substituted furans were prepared in high yields from easily available α-furfurylidenbenzilamines via nucleophilic C-allylation. The homoallylamines obtained this way were used for the synthesis of some polyfunctional aminobutene derivatives. In addition, 4-thiazolidinones some of which are hetaryl substituted at the 2-position were prepared by the reaction of mercapto acids with quinoline carboxaldehydes and p-phenetidine. All new products were fully characterized.Zusammenfassung. Aus den leicht zugänglichen α-Furfurylidenbenzilaminen wurden durch nucleophile C-Allylierung neue Derivative α-substituierter Furane mit hohen Ausbeuten dargestellt. Die dabei gewonnenen Homoallylamine wurden für die Synthese von polyfunktionalen Aminobutenderivaten eingesetzt. Darüber hinaus wurden durch Reaktion von Merkaptosäuren mit Chinolincarboxaldehyden und p-Phenetidin an der 2-Stelle heterosubstituierte 4-Thiazolidinone gebildet. Alle Produkte wurden entsprechend charakterisiert.

Antigenotoxic properties of two newly synthesized β‐aminoketones against N‐methyl‐N′‐nitro‐N‐nitrosoguanidine and 9‐aminoacridine‐induced mutagenesis

The aim of this study was to determine the antigenotoxic potential of two newly synthesized β‐aminoketones against N‐methyl‐N′‐nitro‐N‐nitrosoguanidine (MNNG) and 9‐aminoacridine (9‐AA)‐induced mutagenesis. The mutant bacterial tester strains were MNNG‐sensitive Escherichia coli WP2 uvrA and 9‐AA‐sensitive Salmonella typhimurium TA1537. Both test compounds showed significant antimutagenic activity at various tested concentrations. The inhibition rates ranged from 29.5% (compound 1: 2 mM/plate) to 47.5% (compound 2: 1.5 mM/plate) for MNNG and from 25.0% (compound 2: 1 mM/plate) to 52.1% (compound 2: 2.5 mM/plate) for 9‐AA genotoxicity. Moreover, the mutagenicity of the test compounds was investigated by using the same strains. Neither test compound has mutagenic properties on the bacterial strains at the tested concentrations. Thus, the findings of the present study give valuable information about chemical prevention from MNNG and 9‐AA genotoxicity by using synthetic β‐aminoketones.

Ultrasound-assisted rapid synthesis of β-aminoketones with direct-type catalytic Mannich reaction using bismuth(III) triflate in aqueous media at room temperature

An innovative, powerful, efficient and relatively rapid method was developed to synthesise various β-aminoketone derivatives from cyclohexanone, substituted aromatic amines and aromatic or hetero-aromatic aldehydes via ultrasound-assisted direct-type catalytic Mannich reaction using bismuth(III) triflate in water. Good yields of the desired β-aminoketones were obtained at room temperature by ultrasound-assisted reaction within 1–2 h. The major advantages of the proposed method are undemanding conditions, easy operation, low toxicity, shorter reaction time, anti selectivity and higher yields in comparison with conventional methods.

Three-component aza-Diels–Alder reactions using Yb(OTf)3 catalyst under conventional/ultrasonic techniques

The Yb(OTf)3 catalyzed formal aza-Diels-Alder (or Povarov) reaction of cyclopentadiene and 1,3-cyclohexadiene with in situ-generated N-arylimines under conventional/ultrasonic techniques is herein described. This kind of three-component Povarov reaction results in quinoline and phenanthridine derivatives, which are important biological compounds.

Reactions of the Dianion Obtained by Reductive Metallation of 3,4-Diphenylcinnoline

Summary. The reductive metallation of 3,4-diphenylcinnoline (1) by sodium metal in tetrahydrofuran under an inert atmosphere to the monomeric dianion 2 has been explored, and the nucleophilicity of the disodium adduct towards various protonation, alkylation, and acylation reagents has been investigated. Generally, 2 reacts via its 1,4-positions forming 1,4-dihydro derivatives of 1.Zusammenfassung. Die Herstellung des monomeren Dianions von 3,4-Diphenylcinnolin durch reduzierende Metallierung mit metallischem Natrium in Tetrahydrofuran unter einer inerten Atmosphäre sowie die Nucleophilie dieses Dinatriumaddukts gegenüber verschiedener Protonierungs-, Alkylierungs- und Acylierungsreagenzien wurden untersucht. Das Dianion reagiert durchwegs über die Positionen 1 und 4 zu 1,4-Dihydroderivaten von 3,4-Diphenylcinnolin.

Protective properties of five newly synthesized cyclic compounds against sodium azide and N-methyl-N′-nitro-N-nitrosoguanidine genotoxicity

The current study aims to determine the antimutagenic potential of five newly synthesized cyclic compounds against the genotoxic agents sodium azide (NaN3) and N-methyl-N′-nitro-N-nitrosoguanidine (MNNG). The mutant bacterial tester strains were NaN3-sensitive Salmonella typhimurium TA1535 and MNNG-sensitive Escherichia coli WP2uvrA. According to the results, all the test compounds showed significant antimutagenic activity. The inhibition rates ranged from 26.05% (Compound 4—1 µg/plate) to 68.54% (Compound 5—0.01 µg/plate) for NaN3 and from 32.44% (Compound 3—1 µg/plate) to 60.77% (Compound 5—1 µg/plate) for MNNG genotoxicity. Moreover, the mutagenic potential of the test compounds was investigated using the same strains. The results showed that all the test compounds do not have mutagenic potential on the bacterial strains at the tested concentrations. Thus, the findings of the present study give valuable information about chemical prevention from NaN3 and MNNG genotoxicity.

Aza-Diels–Alder Reactions with Lanthanide Triflates: Syntheses of Quinoline and Phenanthridine Derivatives

Abstract The aza-Diels–Alder reactions of cyclopentadiene and cyclo-1,3-hexadiene with various substituted N-arylimines in the presence of Yb/Sc triflates as catalyst in MeCN at room temperature gave quinoline and phenanthridine derivatives in moderate to high yields. Some of the cycloaddition reactions were carried out in ionic liquid.

(+)-CSA Catalyzed Multicomponent Synthesis of 1-[(1,3-Thiazol-2-ylamino)methyl]-2-naphthols and Their Ring-Closure Reaction under Ultrasonic Irradiation

New 1-[(1,3-thiazol-2-ylamino)methyl]-2-naphthols were obtained by condensation of 2-aminothiazole, aromatic aldehydes, and 2-naphthol in the presence of (+)-camphor-10-sulfonic acid ((+)-CSA) as an effective catalyst under ultrasound-promoted solvent-free conditions. The 1-[(1,3-thiazol-2-ylamino)methyl]-2-naphthol derivatives were converted in ring-closure reaction with formaldehyde to the corresponding naphthoxazine derivatives.