Browse > Article
http://dx.doi.org/10.5012/bkcs.2002.23.3.374

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

Youssif, Shaker
El-Kafrawy, Azza
Bayoumy, Besheer
El-Bahaie, Said
Publication Information
Bulletin of the Korean Chemical Society / v.23, no.3, 2002 , pp. 374-380 More about this Journal
Abstract
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.
Keywords
3,9-Dialkylxanthines; 5-Arylidineamino-; 5-Arylamidouracils; 8-Aryl-3,9-dimethylxanthines;
Citations & Related Records

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