Syntetické postupy vedoucí k 5,6-disubstituovaným pyrazin-2,3-dikarbonitrilům

Bc. Hana Čermáková

Bachelor's thesis

Synthetic procedures leading to 5,6-disubstituted pyrazine-2,3-dicarbonitriles

Abstract:

Ezetimibe, antidiabetics, the intestinal cholesterol absorption inhibitor, acid-base catalysis, basic and acidic hydrolysis, overlap, pH profile.

Abstract:

A literature search focusing on the synthesis of 5,6-disubstituted pyrazine 2,3 dicarbonitriles has been performed. This work mainly focus on the compounds substituted with electron donor N,N-dialkylamino and halogen groups. The halogens can be replaced by the N,N dialkymanino group in terms of nucleophilic aromatic substitution. In general, 5,6 bis(N,N-dialkylamino)pyrazine-2,3-dicarbonitrile 1 can be prepared in a three-step synthesis. This methodology has been experimentally verified in the preparation of 5,6 bis(N,N-dialkylamino)pyrazine-2,3-dicarbonitrile 24. Analogous synthetic preparations of 5,6-bis(4-(N,N-dialkylamino)phenyl)pyrazine-2,3-dicarbonitrile 2 and 5,6 bis(4 bromophenyl)pyrazine-2,3-dicarbonitrile 3 were experimentally verified on the synthesis of particular derivatives such as 5,6-bis(4-(N,N-dimethylamino)phenyl)pyrazine-2,3-dicarbonitrile 25 and 5,6-bis(4-iodophenyl)pyrazine-2,3-dicarbonitrile 26. An exact synthesis of the final derivative, 5,6 bis(4-(N,N-dialkylamino)phenylethynyl)pyrazine-2,3 dicarbonitrile 4, has not been described in the current literature. Four-step synthesis of 5,6-bis(4-(N,N dimethylamino)phenylethynyl)pyrazine-2,3-dicarbonitrile 28 was carried out experimentally.

Keywords

pyrazin, deriváty pyrazin-2, 3-dikarbonitrilů, syntéza, rešerše.

Language used: Czech

Date on which the thesis was submitted / produced: 22. 6. 2011

Thesis defence

• Date of defence: 29. 8. 2011
• Supervisor: doc. Ing. Filip Bureš, Ph.D.

University of Pardubice

Faculty of Chemical Technology

Bachelor programme / field:
Chemistry and Technical Chemistry / Chemistry and Technical Chemistry