Bulletin of the Korean Chemical Society

  • 제23권3호
  • /
  • Pages.374-380
  • /
  • 2002
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

A Novel Synthesis of 3,9-Dialkyl and 8-Aryl-3,9-dimethylxanthines

  • 발행 : 2002.03.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Several compounds of 3,9-dialkylxanthines were prepared from 1-methyl-6-chlorouracil via nucleophillic reactions with different aliphatic amines, followed by nitrosation, reduction, formaylation and finally dehydrocyclization. On the other hands, a series of 8-aryl-3,9-dimethylxanthines were synthesized by dehydrocyclization of 5-arylamido-1-methyl-6-methylaminouracils either by fussion or oxidation of 5-arylidine-amino-1-methyl-6-methylaminouracils using sodium periodate. Phosphoryl chloride was found to be uneffective reagent for dehydrocyclization that, gave another products from 1,3-oxazolo[5,4-d] pyrimidines.

키워드

참고문헌

  1. Hitchings, G. H.; Elion, G. B.; Falco, E. A.; Russel, P. B.;Sherwood, M. B; VanderWerff, H. J. Biol. Chem. 1950, 1, 183.
  2. EIion, G. B.; Hitchings, G. H.; VanderWerff, H. J. Biol. Chem.1951, 192, 505.
  3. Goldner, H.; Dietz, G.; Carstens, E. Annalen 1966, 691, 142. https://doi.org/10.1002/jlac.19666910119
  4. Timmis, G. M.; Cooke, J.; Spickett, R. G. W. Ciba FoundationSymposium on the Chemistry and Biology of Purines; Churchill,London, 1957; p 139.
  5. Taylor, E. C.; Garcia, E. E. J. Am. Chem. Soc. 1964, 86, 4720. https://doi.org/10.1021/ja01075a038
  6. Yoneda, F.; Matsumura, T.; Senga, K. J. Chem. Soc. Chem.Comm. 1972, 606.
  7. Yoneda, F.; Higuchi, M.; Hayakawa, A. Synthesis 1975, 264.
  8. Yoneda, F.; Matsumoto, S.; Sakuma, Y. Chem. and Pharm. Bull.(Japan), 1975, 23, 2425. https://doi.org/10.1248/cpb.23.2425
  9. Yoneda, F.; Sakuma, Y.; Nagamatsu, T.; Mizumoto, S. J. Chem.Soc. Perkin 1 1976, 2398.
  10. Youssif, S.; Pfleiderer W. J. Heterocyclic Chem. 1998, 35, 949. https://doi.org/10.1002/jhet.5570350428
  11. Pfleiderer, W.; Nubel, G. Liebigs Ann. Chem. 1961, 155.
  12. Velkina, N. Ya.; Chaman, E. S.; Ebed, M. Zh. Obshch. Khim.1957, 37, 508.
  13. Okano, T.; Goya, S.; Kaizu, T. J. Pharm. Soc. Japan 1967, 87, 469. https://doi.org/10.1248/yakushi1947.87.5_469
  14. Falco, E. A.; Elion, G. B.; Burgi, E.; Hitchings, G. H. J. Am.Chem. Soc. 1952, 74, 4897. https://doi.org/10.1021/ja01139a049
  15. Elion, G. B.; Burgi, E.; Hitchings, G. H. J. Am. Chem. Soc. 1951,73, 5235. https://doi.org/10.1021/ja01155a070
  16. Fu, S.-C. J.; Chinoporos, E.; Tirzian, H. J. Org. Chem. 1965, 30,1916. https://doi.org/10.1021/jo01017a049
  17. Albert, A.; Brown, D. J. J. Chem. Soc. 1954, 2060. https://doi.org/10.1039/jr9540002060
  18. Traube, W.; Nithack, W. Ber. Dtsch. Chem. Ges. l906, 9, 277.
  19. Jerchel, D.; Krackt, M.; Krucker, K. Liebigs Ann. Chem. 1954,232, 590.
  20. Lichtenberg, D.; Bergmann, F.; Neiman, Z. J. Chem. Soc.(C)1971, 1939.
  21. Itoh, T.; Melik-Obanjanian, R. G.; Ishikawa, I.; Kawabara, N.;Mizuno, Y.; Honma, Y.; Hozumi, M.; Ogura, H. Chem. Pharm.Bull. 1989, 37, 3184. https://doi.org/10.1248/cpb.37.3184
  22. Kazimierczuk, Z.; Shugar, D. Acta Biochim. Polon. 1971, 17, 325.
  23. Goldner, H.; Dietz, G.; Carstons, E. Liebigs Ann. Chem. 1966,692, 134. https://doi.org/10.1002/jlac.19666920117

피인용 문헌

  1. ]pyrimidine vol.181, pp.2, 2006, https://doi.org/10.1080/104265091000642
  2. ChemInform Abstract: A Novel Synthesis of 3,9-Dialkyl and 8-Aryl-3,9-dimethylxanthines. vol.33, pp.34, 2010, https://doi.org/10.1002/chin.200234172
  3. A Novel Synthesis of Fused Uracils: Indenopyrimidopyridazines, Pyrimidopyridazines, and Pyrazolopyrimidines for Antimicrobial and Antitumor Evalution vol.21, pp.12, 2016, https://doi.org/10.3390/molecules21121714
  4. Synthesis, Tautomerism, and Antiradical Activity of Novel Pteridinetrione Derivatives vol.55, pp.4, 2018, https://doi.org/10.1002/jhet.3135
  5. 6-Aminouracils as precursors for the syntheses of fused di- and tricyclic pyrimidines vol.2004, pp.5, 2002, https://doi.org/10.3184/0308234041639683
  6. Synthesis of 3-benzylxanthine and Lumazine Analogues vol.2005, pp.4, 2002, https://doi.org/10.3184/0308234054213438
  7. Synthesis of 2,3-Dihydro-6-methyl-2-thiopyrimidin-4(1H)-one (6-Methylthiouracil) Derivatives and Their Reactions vol.2013, pp.None, 2013, https://doi.org/10.1155/2013/176213