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15N, 13C and 1H NMR study of azo coupling products from diazonium salts and enaminones

✍ Scribed by Vladimír Macháček; Antonín Lyčka; Petr Šimůnek; Tomáš Weidlich

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
111 KB
Volume
38
Category
Article
ISSN
0749-1581

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✦ Synopsis

Reactions of diazonium salts with 4-substituted phenylaminopent-3-en-2-ones produce the corresponding 4-phenylimino-3-phenylhydrazonopentan-2-ones. On the other hand, the reaction of diazonium salt with 4-amino(or 4-methylamino)pent-3-en-2-one gives a mixture of two isomers approaching the tautomeric form of 4-amino-3phenylazopent-3-en-2-ones. The tautomeric form of the individual coupling products was determined by means of 13 C and 15 N NMR chemical shifts and J 15 N,H) coupling constants. With the help of TPPI-NOESY spectra it was possible to follow the rate of mutual exchange of four protons of NH groups in both isomers of 4-amino-3-(4methylphenylazo)pent-3-en-2-one.

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