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Current Organic Synthesis


ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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

Author(s): Ondrej Jandourek, Martin Dolezal and Jiri Kunes

Volume 12, Issue 2, 2015

Page: [189 - 196] Pages: 8

DOI: 10.2174/1570179411999141106101501

Price: $65


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.

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