Decarboxylation of 1,3-dimethylorotic acid revisited: Determining the role of N-l

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 20, 1997, Pages 2623-2628

  Wu, Weiming ^a   Ley Han, Antonio ^a   Wong, Freeman M ^a   Austin, Travis J ^a   Miller, Susan M ^b  

^a SAN FRANCISCO STATE UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIMETHYLOROTIC ACID; OROTIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DECARBOXYLATION; HYDROGEN BOND; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 0030696947     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10028-2     Document Type: Article

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11. 4
12. -1 for citrazinic acid (2) in sulfolane at 206 °C.
13. Tieckelmann, H. In The Chemistry of Heterocyclic Compounds, Pyridine and Its Derivatives, Supplement Part Three; Abramovitch, R. A. Ed.; Wiley: New York, 1974; Chapter XII.
14. a's of protonated 2-pyridone and 4-pyridone have been reported to be 0.75-1.2 and 3.2, respectively, see: (a) Dean, J. A. In Lange's Handbook of Chemistry; McGraw-Hill: San Francisco, 1992; pp 8.19-8.71.
15. (b) Jencks, W. P.; Regienstein, J. In Handbook of Biochemistry and Molecular Biology; Fasman, G. Ed.; CRC: Cleveland, 1976; p 338.
16. Citrazinic acid (2) is more readily protonated than 2-pyridone. For discussions on basicity of related compounds such as glutaconimide, see 13.