The Synthesis of Pyridines, Quinolines and Other Related Systems by the Vilsmeier and the Reverse Vismeier Method

View this article online at wileyonlinelibrary.com.Several new α-alkoxyand α-hydroxyphosphonate derivatives of tetrazole-quinolines were synthesized from the reaction of 2-azidoquinolines 3-carboxaldehyde 1a,b with trialkyl phosphites and dialkyl phosphites. On the other hand, azaphospholes 12a,b were obtained by treating 1a,b with tris(dimethylamino) phosphine. Furthermore, Perkin-type condensation of 1a,b and tetraethyl methylenebisphosphonate provided the corresponding tetrazoloquinoline-based bisphosphonate esters 14a,b. Based on the prediction results (PASS program), the anti-inflammatory activity of the prepared compounds was determined in vivo by the acute carrageenin-induced paw edema in rats. Many of the new compounds exhibit considerable anti-inflammatory properties at a dose of 50 mg/kg body weight. Especially 14a and 14b revealed remarkable activities compared with indomethacin, which was used as a reference standard in this study.

Section: Introductionmentioning

confidence: 99%

Synthesis of Tetrazoloquinoline‐Based Mono‐ and Bisphosphonate Esters as Potent Anti‐Inflammatory Agents

Abdou

Khidre

Shaddy

2013

“…The required 2‐chlorobenzo[ h ]quinoline‐3‐carbaldehyde ( 1 ) was synthesized from a substituted N ‐(1‐naphthyl)acetamide via Vilsmeier–Haack reaction. Compound 1 was converted into the corresponding thione ( 2 ) using potassium sulfide in ethanol .…”

Section: Resultsmentioning

confidence: 99%

The Synthesis of New Benzo[h]thieno[2,3‐b]quinoline‐9‐yl(aryl)methanone Derivatives

Marjani

Khalafy

Rostampoor

2016

Novel derivatives of benzo[h]thieno[2,3‐b]quinoline‐9‐yl(aryl)methanone were synthesized in good yield and short reaction times by reaction of 2‐mercaptobenzo[h]quinoline‐3‐carbaldehyde with phenacyl bromides under basic conditions. All compounds were characterized using Fourier transform infrared, 1H nuclear magnetic resonance and 13C nuclear magnetic resonance, spectral data, and elemental analysis.

“…The reactions of aliphatic substrates [9], particularly carbonyl compounds [10] with chloromethylene iminium salts are highly versatile. They lead to multiple iminoalkylations in the presence of excess reagent and the resulting intermediates undergo cyclization to afford aromatic or heterocyclic compounds [11]. Multifunctional intermediates derived from these reactions ( e.g ., β‐chloroenaldehydes) are subsequently exploited for the synthesis of functionalized heterocycles or other valuable target molecules [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new 2‐aryl‐4‐chloro‐3‐hydroxy‐1H‐indole‐5,7‐dicarbaldehydes via Vilsmeier‐Haack reaction

Eftekhari‐Sis

Zirak

Akbari

et al. 2010

New 2‐aryl‐4‐chloro‐3‐hydroxy‐1H‐indole‐5,7‐dicarbaldehydes were synthesized in three steps from acetophenone derivatives. By oxidation of acetophenones to aryl glyoxals using selenium dioxide and condensation with acetylacetone in the presence of ammonium acetate in water 3‐acetyl‐5‐aryl‐4‐hydroxy‐2‐methyl‐1H‐pyrrols were obtained. 2‐Aryl‐4‐chloro‐3‐hydroxy‐1H‐indole‐5,7‐dicarbaldehydes were synthesized via Vilsmeier‐Haack reaction of pyrrole derivatives in moderate yields. J. Heterocyclic Chem., (2010).