- 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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- A Convenient Synthesis of 1-Alkyl-4-oxo-1,4-dihydrocinnolines
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The reaction of 4-oxo-3-triphenylphosphoranyliden-3,4-dihydro-cinnolines with alkyl halides, followed by basic hydrolysis, affords the title compounds in good yields.These compounds are not easily accessible by other routes.
- Buttero, Paola Del,Licandro, Emanuela,Maiorana, Stefano,Papagni, Antonio
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p. 1059 - 1061
(2007/10/02)
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