Unequivocal Synthesis of Euglenapterin

Journal of Organic Chemistry

Volumn 46, Issue 26, 1981, Pages 5416-5418

  Jacobi, Peter A ^a   Martinelli, Michael ^a   Taylor, Edward C ^b  

^a WESLEYAN UNIVERSITY   (United States)

^b PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845558494     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00339a037     Document Type: Article

References (17)

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2. Böhme, M.; Pfleiderer, W.; Elstner, E.; Richter, W. Angew. Chem., Int. Ed. Engl. 1980, 19, 473.
3. Viscontini, M.; Provenzale, R.; Ohlgart, S.; Mallevialle, J. Helv. Chim. Acta 1970, 53, 1202.
4. Taylor, E. C.; Jacobi, P. A. J. Am. Chem. Soc. 1976, 98, 2301.
5. Taylor, E. C.; Perlman, K. L.; Sword, I. P.; Sequin-Frey, M.; Jacobi, P. A. J. Am. Chem. Soc. 1973, 95, 6407.
6. DeGraw, J.; Brown, V.; Uemura, I. J. Labelled Compd. Radiopharm. 1979, 26, 559.
7. Satisfactory elemental analyes and spectral data were obtained for all new compounds reported. All yields refer to isolated and purified materials, except as noted.
8. Weidenhagen, R. Z. Wirtshaftsgruppe Zuckerind. 1937, 87, 711. Yields for this reaction were found to vary with different samples of cupric acetate. Best results were obtained with material provided by the Fisher Scientific Co.
9. Salomon, L.; Burns, J.; King, C. J. Am. Chem. Soc. 1952, 74, 5161.
10. Hamilton, J.; Smith, F. J. Am. Chem. Soc. 1952, 74, 5162.
11. The stability of such species has recently been commented on: Smith, R. L.; Cochran, D. W.; Gund, P.; Cragoe, E. J., Jr. J. Am. Chem. Soc. 1979, 101, 191.
12. Taylor, E. C.; McKillop, A. “The Chemistry of Cyclic Enaminonitriles and o-Aminonitriles”; Interscience: New York, 1970.
13. Weinstock, J.; Wiebelhaus, V. D. French Patent 1335 354, Aug 16, 1963; Chem. Abstr. 1964, 60, 2975.
14. Other reagents which failed to react with 8 include 2-phenyl-3, 3-dimethylpseudourea, dimethylcyanamide, and tetramethylthiourea.
15. Eilingsfeld, H.; Neubauer, G.; Seefelder, M.; Weidinger, H. Chem. Ber. 1964, 97, 1232.
16. Fachbereich Chemie, Universitat Konstanz, West Germany.
17. Mozingo, R. “Organic Syntheses”; Wiley: New York, 1955; Collect. Vol. III, p 181.