A versatile new synthesis of quinolines and related fused pyridines. Part II.

Meth‐Cohn, Otto; Narine, Bramha; Tarnowski, Brian

doi:10.1016/s0040-4039(01)95334-1

Cited by 61 publications

(18 citation statements)

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“…Yield 2,8-Dichloro-1,7-phenanthroline-3,9-dicarboxylic Acid (8). Similarly to the known procedure [13], to dialdehyde 7 (6.10 g, 20 mmol), suspended in EtOH (96%, 3200 ml), was added AgNO 3 (13.6 g, 80 mmol), dissolved in aqueous EtOH (80%, 200 ml). To the clear solution was added in small portions NaOH (10.0 g, 250 mmol), dissolved in aqueous EtOH (80%, 200 ml), and the dark reaction mixture was stirred at room temperature for 4 h. Then Ag 2 O was filtered off and the filtrate was concentrated almost to dryness under reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR spectrum (300 MHz), δ, ppm: 7.38 (2H, s, H-3,6); 2.25 (6H, s, CH 3 ). 13 C NMR spectrum (75 MHz), δ, ppm (J, Hz): 134.7, 131.5, 130.8 (C-3,6; 1 J = 165.5), 18.7 (CH 3 , 1 J = 128.4).…”

Section: Methodsmentioning

confidence: 99%

“…s, OH); 7.89 (2H, s, H-3,6). 13 (2,5-Dichloro-1,4-phenylene)bis[(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)methanone] (4). To a suspension of pyrazolone 11 (697 mg, 4 mmol) and Ca(OH) 2 (593 mg, 8 mmol) in 1,4-dioxane (6 ml) was added the acid chloride 3 (544 mg, 2 mmol), suspended in 1,4-dioxane (2 ml), and the reaction mixture was heated at reflux for 3 h. After cooling to room temperature, the mixture was treated with 2N HCl (16 ml) and then stirred for 1 h before it was poured onto H 2 O (40 ml).…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR spectrum (300 MHz), δ, ppm 2,8-Dichloro-1,7-phenanthroline-3,9-dicarbaldehyde (7). Similarly to the known procedure [13], POCl 3 (107 g, 0.7 mol) was added dropwise to DMF (21.9 g, 0.3 mol) at 0°C under stirring. To this solution was added the diacetamide 6 (9.61 g, 0.05 mol) and the resulting mixture was refluxed for 4 h. The deeply colored solution was cooled to room temperature and added dropwise to ice water (ca.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of novel polycyclic ring systems containing two pyrano[2,3-c]pyrazol-4-(1H)one moieties

Eller

Wimmer

Hölzer

2007

Chem Heterocycl Comp

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of novel polycyclic ring systems containing two pyrano[2,3-c]pyrazol-4-(1H)one moieties

Eller

Wimmer

Hölzer

2007

Chem Heterocycl Comp

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“…1C) was performed as reported previously [29]. In brief, phosphorus oxychloride (107.31 g) was added to a solution of acetanilide (13.5 g; 1 in Fig.…”

Section: Preparation Of C-(2-chloroquinoline-3-yl)-n-phenyl Nitrone (mentioning

confidence: 99%

C‐(2‐Chloroquinoline‐3‐yl)‐N‐phenyl Nitrone: New Synthetic Antioxidant Inhibits Proliferation and Induces Apoptosis of Breast Carcinoma MCF‐7 Cells

Ramadan

Gamal‐Eldeen²,

Abdel‐Aziz

et al. 2006

Archiv der Pharmazie

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In this work, a new quinoline nitrone derivative, C-(2-chloroquinoline-3-yl)-N-phenyl nitrone (CQPN) was successfully prepared and proved by spectral analysis. The antioxidant activity of CQPN against various radicals was investigated and its anti-cancer properties against different human tumor cell lines including the solid tumor cell lines hepatocarcinoma (Hep-G2) and breast carcinoma (MCF-7); the hematopoietic tumor cell line lymphoblastic leukemia (1301) was also explored. CQPN activities were compared to that of the known nitrone C-phenyl-N-tert-butyl nitrone (PBN). Our results showed that although PBN was the stronger antioxidant than CQPN, the latter was an effective scavenger of different non-physiological (1,1-diphenyl-2-picrylhyrazyl) and physiological (peroxyl and hydroxyl) radicals. Both of CQPN and PBN possess a significant inhibitory property against LPS-stimulated NO production in macrophage. CQPN and PBN treatment resulted in a growth inhibition in Hep-G2 cells (IC50 31.42 microM and 18.6 microM, respectively). Unlike PBN, CQPN strongly inhibited the growth of MCF-7 cells (IC50 14.01 microM) in a dose-dependent manner. On contrary, CQPN and PBN exhibited a proliferative stimulatory activity of the immune cells including macrophages and lymphocytes. Exploring the cytotoxic effect of CQPN against MCF-7 cells indicated that CQPN led to a major time-dependent disturbance in the cell-cycle phases including progressive arrest in both S- and G2/M-phases. This disturbance was found to be associated with a kinetic induction of apoptosis. The novel nitrone derivative CQPN is a strong antioxidant, though less than PBN, and it may be an effective anti-proliferative compound against breast carcinoma.

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The Vilsmeier Reaction of Non‐Aromatic Compounds

Jones

Stanforth

2000

Organic Reactions

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This chapter extends the discussion to reactions between the Vilsmeier‐Haack reagent (subsequently referred to as the Vilsmeier reagent for brevity) and any other compounds in which a carbon‐carbon bond is formed. The discussion thus excludes reactions in which the Vilsmeier reagent acts as a chlorinating agent (for example in the preparation of acid chlorides), or in which it forms carbon‐oxygen or carbon‐nitrogen bonds, unless these are accompanied by formation of a carbon‐carbon bond. For a discussion of the nature of the reagent and of the mechanism of the reaction, the earlier chapter in vol. 49 should be consulted. There are also a number of reviews that deal at length with mechanisms of reactions involving the Vilsmeier reagent, notably those by Jutz and Marson, and hence this chapter will concentrate on applications, with brief mention of mechanisms when necessary. Wizinger has pointed out that alkenes could react with the Vilsmeier reagent, but his only examples were styrenes where the intermediate carbocation has considerable stability. Hydrolysis gives the cinnamaldehyde. In principle, any alkene which is not too sterically hindered can undergo this reaction, but the Vilsmeier reagent has low reactivity as an electrophile, and in practice activation is often necessary. The addition depends on the HOMO of the alkene, and anything increasing the HOMO energy will aid reaction, as for example further conjugation (dienes, trienes, etc.) or the presence of an electron‐donating substituent. Hence aldehydes and ketones are active in their enol forms, and enol ethers and enamines are good substrates. Indeed, all additions covered by this chapter can be regarded as alkene additions, even those on active methyl groups attached to electron‐deficient rings. As with any reaction involving carbocation intermediates, rearrangements are possible; the initial products are sometimes enamines, and this can give rise to polysubstitution. The substrates are grouped into eleven major subsections; references to reviews of particular relevance will be found in the appropriate subsection.

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A versatile new synthesis of quinolines and related fused pyridines. Part II.

Cited by 61 publications

References 0 publications

Synthesis of novel polycyclic ring systems containing two pyrano[2,3-c]pyrazol-4-(1H)one moieties

Synthesis of novel polycyclic ring systems containing two pyrano[2,3-c]pyrazol-4-(1H)one moieties

C‐(2‐Chloroquinoline‐3‐yl)‐N‐phenyl Nitrone: New Synthetic Antioxidant Inhibits Proliferation and Induces Apoptosis of Breast Carcinoma MCF‐7 Cells

The Vilsmeier Reaction of Non‐Aromatic Compounds

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