On the tautomerism of cinnolin-4-ol, cinnoline-4-thiol, and cinnolin-4-amine.

[摘要]：Detailed NMR spectroscopic investigations (1H, 13C, 15N) with cinnolin-4-ol (1) reveal this compd. to exist exclusively in the cinnolin-4(1H)-one form in deuteriodimethyl sulfoxide soln. This finding is confirmed by comparison of the NMR spectroscopic data of 1 with those of the corresponding 'fixed' O-Me and N-Me derivs., 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 addn., in-depth analyses of the NMR spectra of some simple 4-substituted cinnolines are provided.

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