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Volumn 57, Issue 10, 2002, Pages 1881-1890

Improved synthesis of N-substituted 2,3-pyridine-dicarboximides with microwave irradiation

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE; QUINOLINIC ANHYDRIDE; QUINOLINIMIDE; UNCLASSIFIED DRUG;

EID: 0036793202     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-9524     Document Type: Article
Times cited : (15)

References (25)
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  • 7
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    • note
    • Yields of nicotinamides (7) are in certain cases so high that reaction between quinolinic anhydride (4) and anilines in acetic acid has been proposed as a method for the synthesis of N-arylnicotinamides.
  • 8
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    • note
    • A related antecedent is found in the transformation of 2-(N,N-diethylcarbamoyl)pyridine-3-carboxylic acid (main product of aminolysis of quinolinic anhydride (4) with diethylamine) in N,N-diethylnicotinamide. Authors also justify that transformation as a consequence of an isomerization previous to decarboxylation. However, in this case the isomerization mechanism must be different from that proposed by Harrington, since N,N-disubstitution of amide prevents imide formation. Authors suggest in this case an isomerization resulting from intramolecular acidolysis of the amide, similar to that proposed by Kenyon and Norula for the interconversion of quinolinic acid hemiesters.
  • 12
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    • (1999) Tetrahedron , vol.55 , pp. 10851
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    • C. S. Strauss and R. W. Trainor, Aust. J. Chem., 1995, 48, 1675; S. Caddick, Tetrahedron, 1995, 51, 10403; R. A. Abramovitch, Org. Prep. Proced. Int., 1991, 23, 683; H. M. Kingston and S. J. Haswell, 'Microwave-Enhanced Chemistry', American Chemical Society, Washington, DC. 1997; S. Deshayes, M. Liagre, A. Loupy, J.-L. Luche, and A. Petit, Tetrahedron, 1999, 55, 10851. A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault, and D. Mathé, Synthesis, 1998, 9, 1213.
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    • note
    • Opposite to that reported by Rahalkar and Nargund for the reaction of quinolinic anhydride (4) and aniline reaction product proved to be in all cases a mixture of two quinolinamic acids (5 and 6) (see EXPERIMENTAL).


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