Alkylation of 1-[N-(hydroxymethyl)-N-methylamino]-4-quinolones. An improved preparation of intermediates for novel potent tricyclic quinolone antibacterial agents

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 5, 1996, Pages 1371-1376

  Barrett, David ^a   Sasaki, Hiroshi ^a   Kinoshita, Takayoshi ^a   Tsutsumi, Hideo ^a   Sakane, Kazuo ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE DERIVED ANTIINFECTIVE AGENT;

ARTICLE; CRYSTALLOGRAPHY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE;

EID: 0029975276     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.1371     Document Type: Article

References (14)

1. D. Barrett, H. Sasaki, H. Tsutsumi, M. Murata, T. Terasawa, and K. Sakane, J. Org. Chem., 60, 3928 (1995).
2. D. Barrett, H. Tsutsumi, T. Kinoshita, M. Murata, and K. Sakane, Tetrahedron, 51, 11125 (1995).
3. N. Hayashi, Y. Hirao, H. Amano, Y. Ohshita, M. Yokomoto, S. Inoue, and A. Yazaki, "35th Interscience Conference on Antimicrobial Agents and Chemotherapy," San Francisco, 17-21 Sep., 1995, Abstr., F192.
4. a) A. Yazaki, "Abstracts of the Tenth Synthetic Organic Chemistry Symposium (SSOCS-10)," Oct. 20-21, 1993, Hiroshima, Japan, Abstr, pp. 41-44;
5. b) M. Yokomoto, A. Yazaki, N. Hayashi, S. Hatono, S. Inoue, and Y. Kuramoto, European Patent EP 0470578, 1992.
6. For a recent review of the Mannich reaction see: E. F. Kleinman, "The Bimolecular Aliphatic Mannich and Related Reactions," in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon, New York (1991), Vol. 2, pp. 893-951.
7. S. L. Dax and C.-C. Wei. J. Org. Chem., 57, 744 (1992).
8. For an excellent review on hydroxymethylation of amides see: H. E. Zaugg and W. B. Martin, Org. React., (N. Y.), 14, 52 (1965).
9. 3) δ=9.01 (s, 1H), 8.07 (ddd, 1H, J = 2.2, 8.1. 10.1 Hz), 5.47 and 5.43 (each d, 2H total, AB system, J = 11.1 Hz), 4.39 (q, 2H, J = 7.1 Hz), 3.20 (s, 3H), 1.41 (t, 3H, J = 7.1 Hz).
10. Treatment of 4b with sodium hydride in tetrahydrofuran at O °C for 30 min, followed by water quench and adjustment to pH 7 gave after extraction a mixture of 4b and 5b. Trituration with hexane gave a pure sample of 5b.
11. D. Barrett, H. Sasaki, T. Kinoshita, and K. Sakane, J. Chem. Soc., Chem. Commun., 1996, 61.
12. 1)
13. Complete details of the X-ray determination are deposited as Document No. 69027 at the Office of the Editor of Bull. Chem. Soc. Jpn.
14. "SHELXS86: G. M. Sheldrick" in "Crystallographic Computing 3," ed by G. M. Sheldrick, G. Kruger, and R. Goddard, Oxford University Press, (1985), pp. 175-189.