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Microwave-Assisted Synthesis of Pyrazinamide Derivatives: The Coupling Reaction of 3-Chloropyrazine-2-Carboxamide and Ring-Substituted Anilines

[ Vol. 12 , Issue. 2 ]

Author(s):

Ondrej Jandourek, Martin Dolezal and Jiri Kunes   Pages 189 - 196 ( 8 )

Abstract:


A new approach for aminodehalogenation reaction between 3-chloropyrazine-2-carboxamide and ringsubstituted anilines is described. A series of 16 compounds (15 of them novel) derived from pyrazinamide have been synthesized successfully using the advantage of microwave-assisted reaction. The conditions for this aminodehalogenation reaction have been put to investigation to optimize the conversion, yield and time. The final methodology reduces the time needed for reaction from 24 hours using conventional heating to 30 minutes under microwave irradiation and increases the yield. The synthetic procedure together with analytical data of all compounds is presented. Lipophilicity properties were calculated and experimentally determined.

Keywords:

Aminodehalogenation, aniline, carboxamide, heterocycles, microwave synthesis, pyrazinamide, tuberculosis.

Affiliation:

Department of Medicinal Chemistry and Pharmaceutical Analysis, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 50005 Hradec Kralove, Czech Republic.

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