Synthesis of derivatives of new heterocyclic system 5,7-dioxo(4h,6h)-1,3-dithiolo[4,5-d]pyrimidine on the basis of barbituric acid
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The 5-phenyliodonium betaine of barbituric acid reacts with sodium diethyldithiocarbamate to form 5-(diethylaminothiocarbonylthio)barbituric acid, which is cyclized in concentrated H2SO4 solution to form the cation of 5,7-dioxo(4H,6H)-1,3-dithiolo[4,5-d]pyrimidine, isolated in the form of the perchlorate and the chloride. These salts are split by sodium sulflde or selenide, forming 5-[diethylaminothio (seleno)carbonylthio]-4-thiobarbituric acids, which are cyclized by the action of concentrated HCl in an organic solvent to form 5,7-dioxo(4H,6H)-1,3-dithiolo[4,5-d]pyrimidinethione (selenone)-2. The thione and the selenone, as NH acids, form salts; alkylation of the tetrabutylammonium salt affords N(4)-alkyl and N,N′-dialkyl derivatives. The compounds that were obtained have been characterized by IR and PMR spectra.
KeywordsPyrimidine Perchlorate Betaine Thiobarbituric Acid Selenide
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- 1.V. Yu. Khodorkovskii and O. Ya. Neiland, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 2, 131 (1982).Google Scholar
- 2.A. Krief, Tetrahedron, 42, 1209 (1986).Google Scholar
- 3.O. Ya. Neiland and B. Ya. Adamsone, Khim. Geterotsikl. Soedin., No. 6, 848 (1991).Google Scholar
- 4.O. Ya. Neiland and D. é. Neiman, Zh. Org. Khim., 6, 2509 (1970).Google Scholar
- 5.V. I. Slesarev and B. A. Ivin, Zh. Org. Khim., 10, 114 (1974).Google Scholar
- 6.C. L. Angel, J. Chem. Soc., No. 2, 504 (1961).Google Scholar
- 7.O. Ya. Neiland and N. N. Zagorskaya, Khim. Geterotsikl. Soedin., No. 3, 416 (1992).Google Scholar
- 8.V. Zh. Tilika, V. Yu. Khodorkovskii, and O. Ya. Neiland, USSR Inventor's Certificate 1,738,810.Google Scholar