Concise synthesis of ω-fluoroalkylated ketoesters. A building block for the synthesis of six-, seven-, and eight-membered fluoroalkyl substituted 1,2-diaza-3-one heterocycles

Wan, Wen; Hou, Jie; Jiang, Haizhen; Wang, Yangli; Zhu, Shifa; Deng, Hongmei; Hao, Jian

doi:10.1016/j.tet.2009.03.029

Cited by 36 publications

(10 citation statements)

References 37 publications

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“…Under identical reaction conditions, phenylhydrazine failed to yield the corresponding 4,4a,5,6,7,8hexahydro-2,5,7-triarylpyrido[4,3-c]pyridazin-3(2H)-one derivatives 3a-f. However, the reaction was accomplished in dry toluene containing 20 mol% trifluoroacetic acid with moderate to good yields (Scheme 2) [24].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Pyridopyridazin-3(2H)-one Derivatives and Evaluation of Their Cytotoxic Activity against MCF-7 Cells

Selvakumar

Thennarasu

Mandal

2014

ISRN Medicinal Chemistry

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A series of pyridopyridazin-3(2H)-one derivatives was synthesized in two facile steps. Mannich-type three-component condensation afforded the 2,6-diaryl piperidin-4-one derivatives, which underwent intramolecular cyclization in the presence of hydrazine or phenylhydrazine to yield the corresponding pyridopyridazin-3(2H)-one derivatives. All the derivatives of pyridopyridazin-3(2H)-one, except 3e and 3f, showed moderate activity against human breast adenocarcinoma (MCF-7) cells. The higher degree of inhibition of MCF-7 cell proliferation shown by 2a–2f indicates the significance of the amide proton in pyridopyridazin-3(2H)-one derivatives.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Pyridopyridazin-3(2H)-one Derivatives and Evaluation of Their Cytotoxic Activity against MCF-7 Cells

Selvakumar

Thennarasu

Mandal

2014

ISRN Medicinal Chemistry

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“…The synthesis of α‐(trifluoromethyl)pyridazinones 33 was achieved by the condensation of a hydrazine derivative with γ‐keto ester 30 , under acidic conditions . Protonation of 30 with p ‐toluenesulfonic acid produced intermediate 31 , which was then attacked by the hydrazine derivatives to form intermediates 32 .…”

Section: Synthetic Methods To Access α‐(Trifluoromethyl)pyridazinementioning

confidence: 99%

Synthesis of α‐(Trifluoromethyl)pyridazine Derivatives

2018

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Over the last decades, an increasing interest in α‐(trifluoromethyl)pyridazines in medicinal chemistry has been noticed. This interest stems firstly from the recent development of biologically active pyridazines as well as from the capacity of the pyridazine ring to be a bioisoster of other heterocycles. Secondly, due to the influence of a fluorine atom on the chemical and physico‐chemical properties of organic compounds, fluorinated pyridazines have been an attractive scaffold for medicinal chemists. Consequently, the methods that allow the synthesis of fluorinated pyridazines, and more specifically pyridazines possessing either one or two CF3 groups α to the nitrogen atoms, are of great interest and are reported in this review.

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“…For the similar structure, 2-(4-methoxyphenyl)-6-(trifluoromethyl)-4,5-dihydropyridazin-3(2H)-one, see: Wan et al (2009). For conformation analysis of six-membered rings, see: Cremer & Pople (1975).…”

Section: Related Literaturementioning

confidence: 99%

6-Methyl-2-phenyl-4,5-dihydropyridazin-3(2H)-one

2011

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In the title molecule, C11H12N2O, the pyridazine ring has a skew-boat conformation. The dihedral angle between the phenyl ring [r.m.s deviation = 0.0039 (15) Å] and the best mean-plane of the pyridazine ring [r.m.s deviations = 0.2629 (15) Å] is 53.27 (10)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds and C—H⋯π interactions involving the methyl group and the phenyl ring of a symmetry-related molecule.

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Concise synthesis of ω-fluoroalkylated ketoesters. A building block for the synthesis of six-, seven-, and eight-membered fluoroalkyl substituted 1,2-diaza-3-one heterocycles

Cited by 36 publications

References 37 publications

Synthesis of Novel Pyridopyridazin-3(2H)-one Derivatives and Evaluation of Their Cytotoxic Activity against MCF-7 Cells

Synthesis of Novel Pyridopyridazin-3(2H)-one Derivatives and Evaluation of Their Cytotoxic Activity against MCF-7 Cells

Synthesis of α‐(Trifluoromethyl)pyridazine Derivatives

6-Methyl-2-phenyl-4,5-dihydropyridazin-3(2H)-one

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