Synthesis and structure of new 4-amino-1,3,5-triazine-2-thione s-derivatives and their study by 1H, 13C NMR and chromatography-mass spectrometry

4-Amino-1,3,5-triazine-2-thione 1 interacts with allyl bromide, 2-methyl-3-chloro-1-propene, 2,3-dibromopropene-1, prenyl bromide in DMFA/K2CO3 and with cinnamyl chloride, butenyl bromide in DMFA/NaOH to form 4-allylsulfanyl- 2, 4-(2-methylpropene-2-yl)sulfanyl- 3, 4-(2-bromopropene-2-yl)sulfanyl- 4, 4-(2-methylbutene-2-yl)sulfanyl- 5, 4-cinnamylsulfanyl- 6 and 4-(butene-1-yl)sulfanyl-1,3,5-triazine-2-amines 7, respectively. The structure of compounds 2-7 was studied by 1H NMR, as well as of compounds 5 and 7, in their case including 13C NMR; allyl sulfide 2, prenyl sulfide 5 and butenyl sulfide 7 were also studied using chromatography mass spectrometry. In the 1H NMR spectra of compounds 2-7, the weakest field signal in the range of 8.22-8.30 p.p.m. is the signal of the aromatic proton of the triazine cycle, manifested as a singlet. The signals of protons of the S-CH2 group are observed in a strong field - at 3.10-4.19 p.p.m. - depending on the presence of electron donor or electron acceptor groups in the alkenyl fragment. The protons of the =CH2 group are present only in the structure of sulfides 2-4 and 7; they form two signals in the 1H NMR spectra: one signal at 4.85-5.58 p.p.m., the second at 5.03-6.10 p.p.m. In the 13C NMR spectra of prenyl sulfide 5 and butenyl sulfide 7, the carbon atoms of the S-alkenyl groups resonate in the region of strong fields. In the region of weak fields, the signals of aromatic carbon atoms of the 1,3,5-triazine cycle are observed: 182.32-157.95 p.p.m. In the mass spectra of compounds 2, 5 and 7, the characteristic peaks are [M-15]+ and [M-33]+ peaks, the formation of which is associated with the fragmentation of molecular ions undergoing cleavage of the methyl radical and the •SH radical, respectively. The haloalkyl derivative of the heterocyclic series - 2-chloro-1-(2,2,4-trimethyl-4-phenyl-3,4-dihydroquinoline-1(2H)-yl) ethanoate - in reaction with compound 1 has led to the introduction of a new pharmacophore fragment into the simm-triazine molecule, which contributes to the expansion of the spectrum of potential biological activity of its derivatives.