Generation and trapping of 5,6-dimethylenepyrimidin-4-ones in Diels-Alder and Michael additions

Tetrahedron

Volumn 52, Issue 5, 1996, Pages 1723-1734

  Tomé, Augusto C ^a   Cavaleiro, José A S ^a   Storr, Richard C ^b  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIMIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

BETULACEAE;

EID: 0030031867     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01008-4     Document Type: Article

References (20)

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11. Horigome, K.; A. Mizuchi, A.; Awaya, A.; Nakano, T.; Yokoyama, K.; Kato, O.; Kitahara, T.; Imuda, J.; Takey, M. Jpn. Kokai Tokkyo Koho JP 63,246,329; 1988 (C.A. 1989, 111, 63954v).
12. Horigome, K.; A. Mizuchi, A.; Awaya, A.; Nakano, T.; Yokoyama, K.; Kato, O.; Kitahara, T.; Imuda, J.; Takey, M. Jpn. Kokai Tokkyo Koho JP 63,246,329; 1988 (C.A. 1989, 111, 63954v).
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15. 2 from pyrimidine-fused 3-sulfolenes of type 23 were published recently: Tomé, A.C.; Cavaleiro, J.A.S.; Storr, R.C. Tetrahedron Lett., 1993, 34, 6639-6642.
16. Kaneko, C.; Naito, T.; Ito, M. Tetrahedron Lett., 1980, 21, 1645-1648.
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18. Long range coupling constants (JC-H) were optimized to 7.5Hz.
19. We are indebted to Dr. A.M.S. Silva, Dept. of Chem., Univ. of Aveiro, for performing these Selective INEPT experiments.
20. Carbon C5 is easily assigned because in pyrimidines it always appears at higher field (δ 110-120 ppm; 119.1 ppm in compound 30) than any of the other ring-carbons. Brown, D.J. The Chemistry of Heterocyclic Compounds, Vol. 16 (The Pyrimidines, Supplement II), 1985, Chap. 13.