Reaction of acetyltetramic acid with <i>o</i>-phenylenediamine

Abstract

Acetyltetramic acid forms 3-[α-(2-aminophenylamino)ethylidene]-2,4-pyrrolidinedione (Ia) with o-phenylenediamine. NMR spectroscopy showed that compound Ia in solutions of CDCl₃ and DMSO exists as an equilibrium mixture of two rotational isomers caused by hindered rotation around an exocyclic double bond. The analysis of the ¹³C NMR spectra of compounds of type I and the results of quantum chemical calculations indicate preferred chelation of amide carbonyl and predominance of the corresponding rotamer. The reaction of a Ia with hydrochloric acid yields 10-methyl-1H-benzo[b]pyrrolo[3,4-f]-1,4-diazepin-1-one.

How to Cite
Strakov, A. Ya.; Petrova, M. V.; Dishs, A.; Strakova, I. A.; Lakhvich. O. F. Chem. Heterocycl. Compd. 1995, 31, 289. [Khim. Geterotsikl. Soedin. 1995, 336.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01373545