A Convenient Preparation of 4,8-Dimethoxy-3-substituted-2(1H)-quinolones by an Electrophilic Reaction through Base-induced Deprotonation and its Synthetic Application for the Synthesis of New Alkaloids, 3,4,8-Trimethoxy-2(1H)-quinolone and 3-Formyl-4,7,8-trimethoxy-2(1H)-quinolone(Glycocitridine)

Journal of Heterocyclic Chemistry

Volumn 34, Issue 6, 1997, Pages 1677-1683

  Tagawa, Yoshinobu ^a   Kawaoka, Takamitsu ^a   Goto, Yoshinobu ^a  

^a FUKUOKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 FORMYL 4,7,8 TRIMETHOXY 2(1H) QUINOLONE; 3,4,8 TRIMETHOXY 2(1H) QUINOLONE; GLYCOCITRIDINE; N BUTYLLITHIUM N,N,N',N' TETRAMETHYLETHYLENEDIAMINE; QUINOLONE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0031418986     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340606     Document Type: Article

References (14)

1. S. D. Sarker, P. G. Waterman and J. A. Armstrong, J. Nat. Prod., 58, 574 (1995).
2. T-S. Wu, F-C. Chang and P-L. Wu, Phytochemistry, 39, 1453 (1995).
3. H. Tomisawa, R. Fujita, H. Hongo and H. Kato, Chem. Pharm. Bull., 22, 2091 (1974).
4. P. Desos, J. M. Lepagnol, P. Morain, P. Lestage and A. A. Cordi, J. Med. Chem., 39, 197 (1996).
5. T. Kappe and E. Ziegler, Tetrahedron Letters, 1947 (1968).
6. M. Fernández, E. de la Cuesta and C. Avendaño, Synthesis, 1362 (1995).
7. G. H. Posner and K. A. Canella, J. Am. Chem. Soc., 107, 2571 (1985).
8. A. Streitwieser, Jr., Acc. Chem. Res., 17, 353 (1984).
9. G. Queguiner, F. Marsais, V. Snieckus and J. Epsztajn, Adv. Heterocyclic Chem., 52, 238 (1991).
10. T. Moreno, M. Fernández, E. de la Cuesta and C. Avendaño, Heterocycles, 43, 817 (1996).
11. [11a] S. L. Chien and R. Adams, J. Am. Chem. Soc., 56, 1787 (1934);
12. [b] S. A. Mahood and P. V. L. Schaffner, Org. Synth., Coll. Vol., 2, 160 (1943).
13. A. Klemenc, Monatsh. Chem., 33, 701 (1912).
14. N. S. Narasimhan, M. V. Paradkar and R. H. Alurkar, Tetrahedron, 27, 1351 (1971).