Application of the curtius rearrangement in a convenient preparation of 3-amino -pyrazinecarboxylic acid, methyl ester

Synthetic Communications

Volumn 26, Issue 3, 1996, Pages 617-622

  Chen, Jiong J ^a   Hinkley, Jack M ^a   Wise, Dean S ^a   Townsend, Leroy B ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINOPYRAZINECARBOXYLIC ACID METHYL ESTER; PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030020531     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003656     Document Type: Article

References (12)

1. Bariin, G. B., "The Pyrazines, The Chemistry of Heterocyclic Compounds - A Series of Monographs," John Wiley & Sons, New York, 1982, pp. 247-377.
2. Bogert, M. T. and Davidson, D., J. Am. Chem. Soc., 1933, 55, 1667-1668.
3. Weijlard, J., Tishler, M. and Erickson, A. E., J. Am. Chem. Soc., 1945, 67, 802-806.
4. Ellingson, R. C., Henry, R. C. and McDonald, F. G., J. Am. Chem. Soc., 1945, 67, 1711-1713.
5. Buckland, P. R., J. Heterocycl. Chem., 1980, 17, 397-398.
6. Solomons, I. A. and Spoerri, P., J. Am. Chem. Soc., 1953, 75, 679-681.
7. (a) Magnien, E. and Baltzly R., J. Org. Chem., 1958, 23, 2029-2032.
8. (b) Baumgarten, H. E., Smith, H. L. and Staklis, A., J. Org. Chem., 1975, 40, 3554-3561.
9. Smith, P. A. S., "Organic Reactions III," John Wiley & Sons, New York, 1947, pp. 337-450.
10. Jones, R. G., McLaughlin, K. C., "Organic Synthesis, Collective Vol IV," John Wiley & Sons, New York, 1963, pp. 824-827.
11. Moisture will hydrolyze this compound to furnish 2,3-pyrazinedicarboxylic acid.
12. Organic azides may be explosive, thus, caution should be exercised. However, we have not encountered any problems up to a 500 g scale of this reaction in our lab.