- Reactions of cinnoline, cinnoline N-oxides, and their chloro derivatives with alkylamines: The first case of nucleophilic substitution of hydrogen in the cinnoline series
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In contrast to cinnoline and cinnoline N(1)-oxide, cinnoline N(2)-oxide reacts with primary and secondary amines on prolonged heating or in the presence of oxidants to give 3-alkylaminocinnolines.
- Buluchevskaya,Gulevskaya,Pozharskii
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- On the tautomerism of cinnolin-4-ol, cinnoline-4-thiol, and cinnolin-4-amine
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Detailed NMR spectroscopic investigations (1H, 13C, 15N) with cinnolin-4-ol (1) reveal this compound to exist exclusively in the cinnolin-4(1H)-one form in deuteriodimethyl sulfoxide solution. This finding is confirmed by comparison of the NMR spectroscopic data of 1 with those of the corresponding 'fixed' O-methyl and N-methyl derivatives, i.e. 4-methoxycinnoline (3) and 1-methylcinnolin-4(1H)-one (5). Similarly, cinnoline-4-thiol (4) is present in the thione form in deuteriodimethyl sulfoxide, whereas cinnolin-4-amine (7) exists in the amino form. In addition, in-depth analyses of the NMR spectra of some simple 4-substituted cinnolines are provided.
- Holzer, Wolfgang,Eller, Gernot A.,Schoenberger, Simeon
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- Synthesis, structures and biological activity of some 4-amino-3-cinnoline-carboxylic acid derivatives. Part 2
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6,7,8-Substituted 4-amino-3-cinnolinecarboxylic acids 1 were condensed with amines to the corresponding 4-amino-3-cinnolinecarboxamides 7, 8. A variety of pharmacological tests showed a significant CNS activity of some new amides. Decarboxylation of 4-amino-3-cinnolinecarboxylic acids 1 yielded the corresponding 4-aminocinnolines 4 and alkaline hydrolysis of 1 gave 4-oxo-3-cinnolinecarboxylic acids 2. The acids 1 were converted into pyrimido[5,4-c]cinnolines 6 on two ways of synthesis.
- Stanczak,Lewgowd,Ochocki,Pakulska,Szadowska
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- Metallation of diazines XIV. First O-directed metallation of cinnolines. Metallation of 3-, 4-chloro and 3-, 4-methoxycinnolines
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The lithiation of 3-, 4-chloro and 3-, 4-methoxycinnolines was studied and good yields were obtained. When iodine was used as electrophile, 4,8-diiodo or 4,8-iodochloro compounds were prepared. A xanthone and diazepine were synthetized.
- Turck,Ple,Tallon,Queguiner
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p. 13045 - 13060
(2007/10/02)
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