233-62-5Relevant academic research and scientific papers
Synthesis and characterization of some N-Mannich bases of [1,2,3]triazoloquinolines
Ferlin, Maria Grazia,Castagliuolo, Ignazio,Chiarelotto, Gianfranco
, p. 631 - 638 (2007/10/03)
Some novel N-Mannich bases of [1,2,3]-triazolo[4,5-f] and [4,5-h]quinolines were synthesized following the classical experimental procedure for Mannich base preparation: triazoloquinoline with formaldehyde and secondary amine. Tricyclic nuclei were obtained starting from two protected isomeric amino-quinolines, which were nitrated, reduced and diazotated. Two N-anilinomethyltriazoloquinolines were also synthesized via the N-hydroxymethyl intermediate.
Synthesis of triazolo[4,5-f]quinolines. An unusual case of displacement of nitro group in the reaction of 8-acetylamino-6-chloro-5-nitroquinoline with hydrazine and methylhydrazine
Sanna, Paolo,Carta, Antonio,Paglietti, Giuseppe
, p. 693 - 702 (2007/10/03)
Nitration of 1H-, 3-methyl- and 2-methyltriazolo[4,5-f]quinolines (6a-c) as a way to obtain the desired 4-aminotriazolo[4,5-f]quinolines (4) for a medicinal chemistry project was successful only in the case of 6c. Attempted building up of the triazole ring starting from 8-acetylamino-6-chloro-5- nitroquinoline (8) with ammonia, hydrazine and methylhydrazine at 150 °C in ethanol failed. However, the results obtained from these reactions allowed us to observe that, during nucleophilic aromatic substitution of chlorine by these bases an unusual displacement of the nitro group by hydrogen occurred. Comparison of these results with those obtained using different substrates allowed us to evaluate the influence of both para-acetylamino group and pyridine ring in this type of nucleophilic aromatic substitution.
PREPARATION AND SPECTRAL PROPERTIES OF IMIDAZO- AND TRIAZOLOQUINOLINES WITH ANGULAR RING FUSION
Milata, Viktor,Ilavsky, Dusan,Lesko, Jan
, p. 1068 - 1077 (2007/10/02)
The imidazo- and triazoloquinolines (Va, Vb) and imidazo- and triazoloquinolines (Xa, Xb) have been synthetized by the Gould-Jacobs reaction starting from the quinolinecarboxylic acids II and VII prepared by base catalyzed hydrolysis of the esters I and VI, resp.The decarboxylation of the acids II and VII gives the quinolones III and VIII, resp., which are aromatized to the corresponding chloroquinolines IV and IX.The latter compounds give the azoloquinolines V and X on catalytic reduction.The structure of the condensed heterocyclic compounds with angular ring fusion has been proved by 1H and 13C NMR, IR, UV, and mass spectra.
