A One-Step Ring Transformation/Ring Annulation Approach to Pyrrolo[2,3-d]pyrimidines. A New Synthesis of the Pot Inhibitor TNP-351

Journal of Organic Chemistry

Volumn 60, Issue 21, 1995, Pages 6684-6687

  Taylor, Edward C ^a   Patel, Hemantkumar H ^a   Jun, Jong Gab ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

N [4 [3 (2,4 DIAMINO 7H PYRROLO[2,3 D]PYRIMIDIN 5 YL)PROPYL]BENZOYL]GLUTAMIC ACID; PYRROLO[2,3 D]PYRIMIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0028823792     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00126a017     Document Type: Article

References (10)

1. Taylor, E. C.; Kuhnt, D.; Shih, C.; Rinzel, S. M.; Grindey, G. B.; Barredo, J.; Jannatipour, M.; Moran, R. G. J. Med. Chem. 1992, 35, 4450.
2. Miwa, T.; Hitaka, T.; Akimoto, H.; Nomura, H. J. Med. Chem. 1991, 34, 555.
3. For a recent review of such DHFR inhibitors, see: Palmer, D. C.; Skotnicki, J. S.; Taylor, E. C. In Progress in Medicinal Chemistry, Vol. 25; Ellis, G. P., Ed.; Elsevier: Amsterdam, 1988, pp 85-231.
4. For a discussion of these SAR studies, see: Taylor, E. C. Adv. Exper. Med. Biol. 1993, 338, 387.
5. Taylor, E. C.; Young, W. B.; Shih, C. J.; Gossett, L. S., unpublished observations.
6. Taylor, E. C.; McKillop, A. The Chemistry of Cyclic Enamino-nitriles and o-Aminonitriles; Wiley-Interscience: New York, 1970.
7. Gewald, K. Chem. Ber. 1966, 99, 1002.
8. Taylor, E. C.; Gillespie, P.; Patel, M. J. Org. Chem, 1992, 57, 3218.
9. Matsumoto, T.; Ohishi, M.; Inoue, S. J. Org. Chem. 1985, 50, 603.
10. Kaminski, Z. J. Tetrahedron Lett. 1985, 26, 2901.