By R.C. Arridge, P.J. Barham, M. Kawaguchi, J. Kolarik, A. Takuhashi
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Interestingly, only one tautomer (presumably, 97b) was observed in dilute CCl4 solutions of oxazines 97 (X ¼ O) with the order of stabilities being reversed in CDCl3 (80DOK1144). The basicity method was found unacceptable for tautomeric equilibrium studies of thiazines 97 (X ¼ S) (75KG777). The data on the solid-state tautomerism of 97 (X ¼ O, S) are contradictory. Whereas some reports (77KG346) claim that both oxazines and thiazines 97 exist primarily in the amino form, others (80DOK1144) suggest the presence of both amino and imino tautomers as their cyclic homodimers.
Photochromic isomerization of salicylaldehyde 2-quinolylhydrazone 80 involves both amino–imino tautomerism and E– Z isomerizations. When an ethanolic solution of 80a is irradiated in the UV region between 250 and 400 nm at room temperature, it is readily converted into the colored isomer 80b, which is stable in both protic and non-protic solvents at ambient temperature. This conversion presumably occurs via an intramolecular hydrogen transfer from the phenolic group, which precedes the double bond isomerization.
HN R N R N NMe2 NO2 N 81a N H 81b N H 82 According to its 1H NMR spectrum, 9-cyanoaminoacridine 81 (R ¼ CN) exists in solution as amino tautomer 81a; although a rapidly exchanging tautomeric equilibrium cannot be strictly ruled out (84H(22)2595). The tautomeric interconversions in ledakrin, 9-((3-dimethylaminopropyl)imino)1-nitro-9,10-dihydroacridine 82 (1-nitro), and its nitro regioisomers have been extensively investigated. It was shown that the introduction of the 1-nitro group in the heteroaromatic ring system and basic dimethylamino group into the side chain signiﬁcantly affect the equilibrium.
Behavior Of Macromolecules by R.C. Arridge, P.J. Barham, M. Kawaguchi, J. Kolarik, A. Takuhashi