Синтез новых S-производных 4-амино-1,3,5-триазин-2-тиона и их исследование методами ЯМР 1Н, 13С и хромато-масс-спектрометрии

Abstract

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.