Reactions with heterocyclic diazonium salts. Synthesis of several new azolylhydrazones

Hafez, Ebtisam Abdel Aziz; Abed, N. M.; El‐Sakka, Ibrahim A.; Elnagdi, Mohamed Hilmy

doi:10.1002/jhet.5570200206

Cited by 17 publications

(3 citation statements)

References 7 publications

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“…2-Chloro-5-phenylthiazole (2a): Compound 2a was prepared according to the general Stille procedure. Reaction parameters: 20 min; 175 °C; Pd(PPh 3 ) 4 ; benzene.…”

Section: Methodsmentioning

confidence: 99%

Halogenated 2‘-Chlorobithiazoles via Pd-Catalyzed Cross-Coupling Reactions

2006

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Halogenated bithiazoles allow facile further functionalization and are, therefore, suitable intermediates for the synthesis of compounds with interesting biological activity or material science properties. The applicability of three coupling methods (Negishi, Suzuki, and Stille) for the synthesis of the title compounds was compared. The Negishi method proved to be troublesome, and side reactions were predominant. The synthesis of the first thiazoleboronic acid ester offered a new method for the formation of bithiazoles, not generally applicable so far. The lower toxicity compared to that of tin organyls make this method an approach with interesting perspectives. The Stille coupling proved to be superior to the other methods and enabled the synthesis of the title compounds with diverse connectivity.

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“…2-Chloro-5-phenylthiazole (2a): Compound 2a was prepared according to the general Stille procedure. Reaction parameters: 20 min; 175 °C; Pd(PPh 3 ) 4 ; benzene.…”

Section: Methodsmentioning

confidence: 99%

Halogenated 2‘-Chlorobithiazoles via Pd-Catalyzed Cross-Coupling Reactions

2006

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“…Compound 15 also showed excellent dog pharmacokinetics (Table 3), with a long half-life, low clearance and an excellent oral bioavailability. This optimal profile is dependent on the acetamide as either an unsubstituted piperazine (16) or a morpholine (17) produced compounds that were still potent but had slightly greater affinity for hERG and significantly poorer dog pharmacokinetics (Cl ) 24.2 and 12.4 mL/ min/kg, respectively, Table 3). The acetamide however could be replaced by other polar carbonyl-containing moieties to maintain or enhance the profile.…”

Section: Resultsmentioning

confidence: 99%

“…4-(tert-Butyldimethylsilanyloxymethyl)pyridin-2-ylamine (1.00 g, 4.19 mmol) was dissolved in 20 mL of anhydrous THF at room temp, and NaH (60% dispersion, 0.670 g, 16.8 mmol) was added. When the bubbling stopped, 2-chloro-5-phenylthiazole 16 0.739 g (3.78 mmol) was added, and the reaction was heated to reflux. After 2 h the THF was removed in vacuo, and the resulting solution was taken to neutral pH with 1 M HCl (aq) and filtered.…”

Section: -({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridine (4)mentioning

confidence: 99%

Potent N-(1,3-Thiazol-2-yl)pyridin-2-amine Vascular Endothelial Growth Factor Receptor Tyrosine Kinase Inhibitors with Excellent Pharmacokinetics and Low Affinity for the hERG Ion Channel

et al. 2004

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A series of N-(1,3-thiazol-2-yl)pyridin-2-amine KDR kinase inhibitors have been developed that possess optimal properties. Compounds have been discovered that exhibit excellent in vivo potency. The particular challenges of overcoming hERG binding activity and QTc increases in vivo in addition to achieving good pharmacokinetics have been acomplished by discovering a unique class of amine substituents. These compounds have a favorable kinase selectivity profile that can be accentuated with appropriate substitution.

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Studies on 3,5‐Diaminopyrazoles: Synthesis of New Polyfunctionally Substituted Pyrazoloazines and Pyrazoloazoles

Ibrahim

Sadek

Abdel-Al

1987

Archiv der Pharmazie

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New aminopyrazolo[ 1,5-a]pyrimidines, pyrazolo[ 3,4-dlpyrimidines and imidazof 1,2-blpyrazoles were synthesised from ethyl 3,5-diaminopyrazole-4-carboxylate (1). Studien iiber 3,5-Diaminopyrazole: Synthese neuer polyfunktionell substituierter Pyrazolazine und PyrazoloazoleEinige neue Aminopyrazolol l,S-alpyrimidine, Pyrazolo[ 3,4-dlpyrimidine und Imidazo[1,2-blpyrazole wurden aus 3,5-Diamino-4-ethoxycarbonylpyrazol(l) hergestellt.Pyrazolo[ 1,5-alpyrimidine derivatives are important due to their ability to inhibit 3',5'-cyclic AMP phosphodiesterase and their cardiotropic properties'. 2). Moreover, antipyretic, antiinflammatory and anticancer activities have been reported for many pyrazolo[ 1,5-alpyrimidine derivative^^.^).

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Reactions with heterocyclic diazonium salts. Synthesis of several new azolylhydrazones

Abstract: Several new stable azolylhydrazones could be synthesized via coupling of diazotised cycliuc amidines with active methylene reagents. The obtained compounds were utilised for synthesis of several, otherwise not readily accessible fused azoles.

Cited by 17 publications

References 7 publications

Halogenated 2‘-Chlorobithiazoles via Pd-Catalyzed Cross-Coupling Reactions

Halogenated 2‘-Chlorobithiazoles via Pd-Catalyzed Cross-Coupling Reactions

Potent N-(1,3-Thiazol-2-yl)pyridin-2-amine Vascular Endothelial Growth Factor Receptor Tyrosine Kinase Inhibitors with Excellent Pharmacokinetics and Low Affinity for the hERG Ion Channel

Studies on 3,5‐Diaminopyrazoles: Synthesis of New Polyfunctionally Substituted Pyrazoloazines and Pyrazoloazoles

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