N- vs. S-PTC alkylation of 5-carboethoxy-2-thiouracil and its reactivity towards some nucleophilic reagents

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 178, Issue 11, 2003, Pages 2497-2504

  Hassan, M A ^a,b   Mohamed, M M ^a   Shiba, S A ^a   Abou El Regal, M K ^a   Khalil, A ^a  

^a AIN SHAMS UNIVERSITY   (Egypt)

^b KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

5 Carboethoxy 2 thiouracil; phase transfer catalysis (PTC); Pyrimidothiazine; Thiazolopyrimidine

Indexed keywords

5 CARBOETHOXY 2 THIOURACIL; HYDRAZINE; HYDROXYLAMINE; IODINE DERIVATIVE; METHYLMAGNESIUM IODIDE; ORGANOHALOGEN DERIVATIVE; REAGENT; THIOURACIL DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKYLATION; ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0344688352     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/714040963     Document Type: Article

References (19)

1. S. A. Shiba, N. M. S. Harb, M. A. El-Kasaby, M. A. Hassan, and M. K. Abou El-Regal, Phosphorus, Sulfur, and Silicon, 104, 15 (1995).
2. M. A. Hassan and D. Döpp, Heterocycles, 45, 451 (1997).
3. M. A. Hassan, M. M. Mohamed, and S. A. Shiba, Phosphorus, Sulfur, and Silicon, 157, 97 (2000).
4. S. A. Shiba, M. M. Mohamed, M. A. Hassan, and A. M. El-Sayed, Phosphorus, Sulfur, and Silicon, 158, 91 (2000).
5. M. Lissel, S. Schmidt, and B. Neumann, Synthesis, 382 (1986).
6. H. J.-M. Dou, P. Hassanaly, and J. Metzger, J. Heterocycl. Chem., 14, 321 (1977).
7. H. J.-M. Dou, P. Hassanaly, J. Kister, G. Vernin, and J. Metzger, Helv. Chim. Acta, 61, 3143 (1978).
8. P. Hassanaly, H. J.-M. Dou, and M. Ludwikow, Bull. Soc. Chim. Belg., 91, 661 (1982).
9. R. H. Koppel, R. H. Springer, R. K. Robins, and C. C. Cheng, J. Org. Chem., 27, 3614 (1962).
10. a) A. Palumbo and M. d'Ischia, Biochem. & Biophys. Res. Comm., 282, 793 (2001);
11. b) D. M. Saleh, G. K. Barrel, C. I. Bailey, and C. M. A. Frampton, Small Ruminant Research, 30,49 (1998).
12. a) H. Armstrong et al. (Merck and Co., Inc., USA). WO 0100213, A1 20010104 (2001); Chem. Abstr., 134, 12273 (2001);
13. a) H. Armstrong et al. (Merck and Co., Inc., USA). WO 0100213, A1 20010104 (2001); Chem. Abstr., 134, 12273 (2001);
14. b) M. Barvian et al., J. Med. Chem., 43, 4606 (2000);
15. D. H. Kim, J. Heterocycl. Chem., 22, 173 (1985);
16. R. S. Shadbolt and T. L. Ulbricht, J. Chem. Soc., 13, 1172 (1967).
17. D. Landini, F. Montanari, and A. Maia, J. Amer. Chem. Soc., 100, 2796 (1978).
18. J. E. Gorden and R. Z. Kutina, J. Amer. Chem. Soc., 99, 3903 (1977).
19. Yu. M. Volovenko and E. V. Blyumin, Khim. Geterotsikl. Soedin (in English), 33, 1696 (1998).