5,7-DICHLORO-1,3-DITHIOLO-[4,5-<i>d</i>]PYRIMIDINE-2-THIONE AND -2-SELONE: SYNTHESIS, CRYSTAL STRUCTURE, SOLVATOCHROMISM, AND REACTIONS WITH NUCLEOPHILES
Keywords:
1,3-dithiolo[4,5-d]pyrimidines, crystal structure, nucleophilic substitution in chloropyrimidines, solvatochromism of thiones and selonesAbstract
We have obtained for the first time the halo derivatives of a novel heterocyclic system, 1,3-dithiolo-[4,5-d]pyrimidine-2-thione and -2-selone, by reaction of 5,7-dioxo(4H,6H)-1,3-dithiolo[4,5-d]-pyrimidine-2-thione and -2-selone with POCl3. The crystal structure of thione confirms that we had obtained the desired compound. The electronic absorption spectra reveal an interesting solvatochromism connected with the appearance of low-intensity n→π transitions from selenium and sulfur atoms in the visible region of the spectrum. The chlorine atoms in the studied compounds have significant mobility in reactions with nucleophiles (amines, thiourea, azidione), which ensures that new derivatives of 1,3-dithiolo[4,5-d]pyrimidine-2-selone are obtained, and specifically 7-N,N-dialkylamino, 7-N-alkyl-N-arylamino derivatives and 7-isothiuronium salts. The 2-selones obtained can be used in synthesis of new tetrathiafulvalenes.
How to Cite
Neilands, O.; Valters, R.; Belyakov, S. V. Chem. Heterocycl. Compd. 2002, 38, 79. [Khim. Geterotsikl. Soedin. 2002, 87.]
For this article in the English edition, see DOI https://doi.org/10.1023/A:1014811527518
