Über die Synthese von Pyrazolaldehyden I

Rojahn, C. A.; Seitz, Alexander

doi:10.1002/jlac.19234340114

Cited by 16 publications

(9 citation statements)

References 4 publications

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“…All reactions were monitored by TLC on silica gel coated aluminum sheets (Silica Gel 60 F254, Merck). Compounds (1), (4), and (5) were prepared according to literature procedure [22][23][24][25][26][27] with m.p. 120-122 o C, 144-146 o C and 214-216 o C, respectively.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Reactions and Spectral Characterization of Novel Thienopyrazole Derivatives

Ahmed¹,

Eldean²,

Zaki³

et al. 2018

ECB

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4-Amino-3-methyl-1-phenyl-1H-thieno[2,3-c]pyrazole-5-carboxamide has been synthesized by an innovative method. The aminoamide derivative was gently refluxed with chloroacetyl chloride under neat conditions followed by neutralization with sodium carbonate solution to afford the chloromethyl pyrimidinone compound. The chloromethyl pyrimidinone derivative was converted to the thiol derivative by the reaction with thiourea in ethanol. The thiol compound was alkylated with α-halocompounds such as ethyl chloroacetate, chloroacetone, phenacyl bromide and 2-chloro-4,6-dimethylnicotinonitrile to afford the corresponding S-alkylated compounds. The chemical structures of the newly synthesized compounds were elucidated on the basis of elemental and spectral analyses containing FT-IR, 1 H-NMR, and mass spectroscopy.

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Section: Methodsmentioning

confidence: 99%

Synthesis, Reactions and Spectral Characterization of Novel Thienopyrazole Derivatives

Ahmed¹,

Eldean²,

Zaki³

et al. 2018

ECB

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“…72–73 ºC (lit. [47] m.p. 74 ºC); 1 H-NMR (500 MHz, CDCl 3 ): δ (ppm) 7.41 (m, 2H, Ph H-2,6), 7.36 (m, 2H, Ph H-3,5), 7.30 (m, 1H, Ph H-4), 4.24 (q, 7.1 Hz, 2H, OCH 2 ), 2.43 (s, 3H, 3-Me), 1.27 (t, 7.1 Hz, 3H, Me); 13 C-NMR (125 MHz, CDCl 3 ): δ (ppm) 161.9 (CO, 3 J (CO,CH 2 ) = 3.1 Hz), 151.7 (C-3, 2 J (C-3,3-Me) = 7.0 Hz), 137.2 (Ph-C-1), 130.8 (C-5), 128.7 (Ph C-3,5), 128.5 (Ph C-4), 125.1 (Ph C-2,6), 109.8 (C-4, 3 J (C-4,3-Me) = 2.7 Hz), 59.9 (OCH 2 , 1 J = 147.6 Hz, 2 J (O C H 2 ,C H 2 ) = 4.4 Hz), 14.4 (3-Me, 1 J = 129.2 Hz), 13.9 (ester-Me, 1 J = 127.0 Hz, 2 J ( C H 3 ,C H 2 ) = 2.6 Hz); 15 N-NMR (50 MHz, CDCl 3 ): δ (ppm) −168.2 (N-1), −77.6 (N-2); MS m/z (%): 264/266 (M + , 53/18), 219 (100), 155 (12), 77 (56), 51 (26).…”

Section: Methodsmentioning

confidence: 99%

Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data

et al. 2010

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The synthesis of the title compounds is described. Reaction of 1-substituted 2-pyrazolin-5-ones with 5-chloro-1-phenyl-1H-pyrazole-4-carbonyl chloride or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride, respectively, using calcium hydroxide in refluxing 1,4-dioxane gave the corresponding 4-heteroaroylpyrazol-5-ols, which were cyclized into 1H-pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones by treatment with K2CO3/DMF. The latter were converted into the corresponding thiones upon reaction with Lawesson’s reagent. Detailed NMR spectroscopic investigations (1H, 13C, 15N) of the ring systems and their precursors are presented.

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“…5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde ( 2 ) [33]. Phosphorus oxychloride (250 mmol) was added dropwise into N , N -dimethylformamide (100 mmol) at 0–5 °C.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, DFT Study and Antifungal Activity of Pyrazolecarboxamide Derivatives

Shi

Yang

et al. 2016

Molecules

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A series of novel pyrazole amide derivatives were designed and synthesized by multi-step reactions from phenylhydrazine and ethyl 3-oxobutanoate as starting materials, and their structures were characterized by NMR, MS and elemental analysis. The antifungal activity of the title compounds was determined. The results indicated that some of title compounds exhibited moderate antifungal activity. Furthermore, DFT calculations were used to study the structure-activity relationships (SAR).

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Über die Synthese von Pyrazolaldehyden I

Cited by 16 publications

References 4 publications

Synthesis, Reactions and Spectral Characterization of Novel Thienopyrazole Derivatives

Synthesis, Reactions and Spectral Characterization of Novel Thienopyrazole Derivatives

Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data

Design, Synthesis, DFT Study and Antifungal Activity of Pyrazolecarboxamide Derivatives

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