Abstract:1295 1957 Phthalmonopersaure (1 Mol.) in 100 ccm Ather gegeben und das Reaktionsgemisch Uber Nacht im Kuhlschrank aufbewahrt. Einen Teil der sich bei der Reaktion bildenden Phthalsiiure filtriert man ab und dampft die ather. Lbsung i. Vak. zur Trockne ein. In der Aufschltimmung des gepulverten RUckstandes in 250 ccm Chloroform lbst sich das Sulfoxyd, wahrend der Rest der Phthalsaure ungelbst zuruckbleibt. Nach Entfernen des Chloroforms hinterbleibt ein weiDes Kristallpulver, das man aus Ather-Aceton umkristall… Show more
“…Thiazolo[5,4- b ]quinoline derivatives were previously obtained by different methods which can be related to synthetic pathways I−III (Scheme ). Tanasescu et al . , have reported the synthesis of 2-(arylamino)- and 2-(alkylamino)thiazolo[5,4- b ]quinolines in low yields (50−60%) by condensation of primary or secondary amines with 2-chloro-3-isothiocyanatoquinolines which were used as precursors of 12 (Scheme , pathway I). Quinolines 13 have been obtained from 2-mercapto-3-aminoquinolines and transformed into thiazoloquinolones 11 with low yields (35−60%) (Scheme , pathway II).…”
Section: Resultsmentioning
confidence: 99%
“…Among all these derivatives, thiazolo[4,5- g ]-, -[5,4- g ]-, -[4,5- h ]-, -[5,4- h ]-, -[4,5- f ]-, and [5,4- f ]quinolines 9 1 (Chart ) have shown high activity as antibacterial agents. On the other hand, the synthesis of thiazolo[5,4- b ]quinoline derivatives 2 has rarely been reported in the literature. − These compounds have been described as potential antispasmodics, precursors of symmetrical cyanines, antiinflammatories, and fluorescent probes (Chart ). 1 …”
A new synthesis of 9-hydroxy- and 9-(alkylamino)thiazolo[5,4-b]quinolines by cyclization of 4-(ethoxycarbonyl)-5-(arylamino)thiazoles and 5-(arylamino)-4-carbamoylthiazoles, respectively, is described. In vitro cytotoxicity of a large number of derivatives of these compounds has been tested against several cell lines. The highest activities observed are associated with the presence of a 2-[[(N,N-diethylamino)ethyl]amino] substituent at C-2 and a fluorine atom at the C-7 position of the tricyclic planar heteroaromatic framework. Three structural features seem to be essential for antitumor activities: a positive charge density at carbon C-7, a side chain at position C-2 or C-9 of the thiazoloquinoline skeleton with two basic nitrogens and a pKa value of 7.5-10 in the most basic center, and a conformational flexibility of this basic side chain. These structural requirements must be simultaneously satisfied in order to ensure a significant antitumor activity.
“…Thiazolo[5,4- b ]quinoline derivatives were previously obtained by different methods which can be related to synthetic pathways I−III (Scheme ). Tanasescu et al . , have reported the synthesis of 2-(arylamino)- and 2-(alkylamino)thiazolo[5,4- b ]quinolines in low yields (50−60%) by condensation of primary or secondary amines with 2-chloro-3-isothiocyanatoquinolines which were used as precursors of 12 (Scheme , pathway I). Quinolines 13 have been obtained from 2-mercapto-3-aminoquinolines and transformed into thiazoloquinolones 11 with low yields (35−60%) (Scheme , pathway II).…”
Section: Resultsmentioning
confidence: 99%
“…Among all these derivatives, thiazolo[4,5- g ]-, -[5,4- g ]-, -[4,5- h ]-, -[5,4- h ]-, -[4,5- f ]-, and [5,4- f ]quinolines 9 1 (Chart ) have shown high activity as antibacterial agents. On the other hand, the synthesis of thiazolo[5,4- b ]quinoline derivatives 2 has rarely been reported in the literature. − These compounds have been described as potential antispasmodics, precursors of symmetrical cyanines, antiinflammatories, and fluorescent probes (Chart ). 1 …”
A new synthesis of 9-hydroxy- and 9-(alkylamino)thiazolo[5,4-b]quinolines by cyclization of 4-(ethoxycarbonyl)-5-(arylamino)thiazoles and 5-(arylamino)-4-carbamoylthiazoles, respectively, is described. In vitro cytotoxicity of a large number of derivatives of these compounds has been tested against several cell lines. The highest activities observed are associated with the presence of a 2-[[(N,N-diethylamino)ethyl]amino] substituent at C-2 and a fluorine atom at the C-7 position of the tricyclic planar heteroaromatic framework. Three structural features seem to be essential for antitumor activities: a positive charge density at carbon C-7, a side chain at position C-2 or C-9 of the thiazoloquinoline skeleton with two basic nitrogens and a pKa value of 7.5-10 in the most basic center, and a conformational flexibility of this basic side chain. These structural requirements must be simultaneously satisfied in order to ensure a significant antitumor activity.
“…The synthesis of such compounds is typically multistep and complicated [10–12] . Therefore, there is a demand for general and straightforward methods for their creation is in demand.…”
An operationally simple approach to azolo[4,5‐b]quinolines based on the condensation of 2‐aminobenzaldehydes with various azolones is developed. A series of 22 compounds was synthesized typically in good yields (40–92 %).
“…For example, quinoline-2-thiones have been investigated from a variety of viewpoints, such as synthetic intermediates, biologically active compounds, sulfur−nitrogen mixed donor ligands, and protective groups of thiols . The synthesis of quinoline-2-thiones is usually achieved by thiation of corresponding quinoline-2-ones 2,5 or 2-haloquinolines. 1a, However, direct synthetic methods that involve construction of a quinoline skeleton with simultaneous introduction of a thiocarbonyl have hardly been reported so far . From our ongoing interests in the synthesis of nitrogen-containing heterocycles using functionalized azacumulenes as key intermediates, we envisioned that a tandem nucleophilic reaction−cyclization of N -(2-alkynylphenyl)isothiocyanate 9 would be a convenient synthetic method for quinoline-2-thiones if the nucleophile first attacks the alkyne and a subsequent cyclization involving the cumulene function occurs (Scheme ).…”
A new approach to the synthesis of 4-aryl- or 4-arylthioquinoline-2-thiones via indium(III) reagent-mediated tandem Friedel-Crafts alkenylation-cyclization of 2-alkynylphenyl isothiocyanates is described.
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