Synthesis of condensed S-, N- containing heterocyclic systems on the base of 2-amino-4,9-dioxo-4,9-dihydronaphto[2,3-b]thiophene-3-ethylcarboxilate

Authors:

Maryna Stasevych, Svitlana Sabat, Rostyslav Musyanovych and Volodymyr Novikov

Synthesis of a new 2-aryl-4Н-naphtho[2’,3’,4,5]thieno[2,3-d][1,3]oxazine-4,5,10-triones, 2-arylnaphtho[2’,3’,4,5]thieno[2,3-d][1,3]pyrimidine-4,5,10(3Н)-triones, 3-phenyl naphtho[2’,3’,4,5]thieno[2,3-d][1,3]pyrimidine-2,4,5,10(1Н, 3Н)-tetraone and 2-thioxo-2,3-dyhydronaphth[2’,3’,4,5]thieno[2,3-d]pyrimidine-4,5,10(1Н)-trione was carried out. The mechanism of 2-aryl-4Н-naphtho[2’,3’,4,5]thieno[2,3-d][1,3]oxazine-4,5,10-triones formation was suggested.

3-b]thiophene-3-ethylcarboxilate

[1] Miyaki K. and Ikeda N.: J. Pharm. Soc. Japan., 1953, 73, 961.
[2] Ryu, Chung Kyu. et al.: Chem.Abst., 1994, 121, 541.
[3] Sextion W.: Chem.consist. and biol. Activitie, London 1953.
[4] Haychi S. Kumamoto: Pharm.Bull.,1954, 1, 93.
[5] Litvinenko L.: Zaschita nefteproductov ot dejstviya mikroorganizmov. Khimiya, Мoskwa 1977.
[6] Colwell C. and Mocall M.: J. Bac.,1946, 51, 659.
[7] Marrian D., Friedmann E. and Ward I.: Biochem. J., 1953, 54, 65.
[8] Ikeda N.: J.Pharm. Soc.Japan., 1955, 75, 1073.
[9] Melnikov N., Novozhylov K. and Velan S.: Spravochnik po pestitsidam. Khimiya, Мoskwa 1985.
[10] Fesen Mark R. Kohn Kurt W. and Leteurte F.: Chem.Abst., 1994, 121, 672.
[11] Deriu I. and Benesch H.: Bull. Soc. Chim.Biol., 1962, 44, 91.
[12] Oeriu I. and Cracea M.: Zh. Оbsch. Khimii., 1963, 33, 1127.
[13] Vechio G., Napoli A. and Biondi E.: Chem.Abst., 1950, 44, 2072.
[14] Kowalik R.: Prace glown. Inst. chem. przmysl., 1951, 2, 51.
[15] Fieser L., Berliner E., Bondhus F. et al.: J. Am. Chem. Soc., 1948, 70, 3151.
[16] Ragazze E., De Biasi M., Pandolfo L., Chenillato A. and Capparota L.: Chem. Abst., 1993, 119, 58.
[17] Taylor E. and Wong G.: J. Org. Chem., 1989, 54, 3618.
[18] Taylor E. and Ray P.: J. Org. Chem., 1988, 53, 35.
[19] Taylor E.; George, T., Fletcher S., Tseng C. and Harrington P.: J. Org. Chem., 1983, 48, 4852.
[20] Taylor E.: J. Heterocycl. Chem., 1990, 27, 1.
[21] Taylor E. and Reiter L.: J.Am. Chem. Soc., 1989, 111, 285.
[22] Taylor E., Jacobi P. and Martinelli M.: J. Org. Chem., 1981, 46, 5416.
[23] Taylor E., Ray P.: J. Org. Chem., 1991, 56, 1812.
[24] Taylor E., Ray P.: J. Org. Chem., 1987, 52, 3997.
[25] Taylor E., Perlmann K., Kim Y. et al.: J. Am. Chem. Soc., 1973, 95, 6413.
[26] Кanischev О., Sabat S., Musyanovych R. and Novikov V.: Visnyk NU “LP”. Khimiya, tehnologiya rechovyn ta yh zastosyvannya”, 2004, 589, 78.