The synthesis and properties of 4-substituted pyrrolidine-2,3-Diones

The previous work on the synthesis and properties of pyrrolidin-2,3-diones is discussed particularly with regard to the effect that a 4-substituent can have upon the ketone function at position 3. The synthesis of a series of 4-substituted pyrrolidin-2,3-diones is described and the structure and 3-ketone function studied by infra-red, ultra-violet and NMR spectroscopy. The reactivity of this ketone position is examined in suitable compounds by reaction with hydrazine and ethylene diamine. The 4-benzylidene, 4-carbethoxy and 4-cyano compounds are of particular interest since they might be expected to facilitate the formation of the enol at C3. The spectroscopic features and reactions of these compounds show that they additionally have the expected ketone function at position 3. Confirmation of this result is provided by the reaction of the 2,3-diones with o-phenylenediamine with which may form quinoxalines. A 4-carbethoxypyrrolidine -2,-3-dione will react with o-phenylenediamine win two ways forming wither a quinoxaline type structure or a diazacycloheptadiene ring. Structures are assigned to these compounds on analytical and spectral evidence and the conditions for each type of reaction and its mechanism are discussed. The 4-benzylidene-1-benzyl-2-3-dioxopyrrolidines also react with o-phenylene-diamine to form a diazacycloheptadiene ring. The NMR spectra of these compounds are discussed. The 4-cyano-2-3-dioxopyrrolidines have been converted to the corresponding ketones by a Grignard reaction.

Name dc:type.qualificationname

PhD

Level dc:type.qualificationlevel

Doctoral

Grantor dc:publisher.institution

De Montfort University

Year dc:date.issued

1981

Author dc:creator

• Mumford, Frank Robert

Licence

• https://dora.dmu.ac.uk/bitstreams/e025273a-f7d6-48ff-b28a-1d4e8b7102a7/download