A relation between the bonded NH stretching frequencies of primary amides

Ramiah, K. Venkata; Chalapathi, V. Venkata

doi:10.1016/0022-2852(64)90013-x

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1995

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Ringspaltung von 4-(4-Nitrophenylazo)-substituierten Pyrazolidin-3,5-dion - Derivaten zu ?-(4-Nitrophenylhydrazono)semicarbaziden und Folgeprodukten

1995

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Ring Cleavage of 4‐(4‐Nitrophenylazo)‐substituted Pyrazolidine‐3,5‐diones to α‐(4‐Nitrophenylhydrazono)semicarbazides with Consecutive Reactions The reaction of 1 and 2 with ammonia, methylamine and dimethylamine in aprotic solvents, e. g. diethyl ether, yields the compounds 3 – 8 which can exist in two isomeric forms (form a/b). On conditions which are usually chosen for spectroscopic investigations only form a could be detected. Nevertheless, under the influence of bases like KOH or ammonia in water or alcohol these compounds are mainly converted to semicarbazides (11–15) which means that this reaction must run via form b. Those semicarbazides which are unsubstituted at the N‐4 of their semicarbazide‐moiety show great tendency to cyclize, thus forming the triazolederivatives 16–18. In contrast to these products, in the case of the N‐4‐monomethylated semicarbazide 14 the six‐membered heterocyclus 19 was obtained. In comparison with 1 and 2, stable intermediates such as 3–8 in the reaction with 21 could not be isolated.

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