Синтез и строение 6-амино-5-нитро-2-пропаргилсульфанил-4(3н)-пиримидинона

E. V. Artem’eva; K. Yu. Petrova

Authors

E. V. Artem’eva South Ural State University
K. Yu. Petrova South Ural State University

Keywords:

6-amino-5-nitro-2-propargylsulfanyl-4(3H)-pyrimidinone, oxidation, structure, X-ray diffraction analysis, IR spectroscopy, 1H NMR spectroscopy

Abstract

6-Amino-5-nitro-2-propargylsulfanyl-4(3H)-pyrimidinone (1) has been synthesized for the first time by the reaction of 6-amino-5-nitroso-2-propargylsulfanyl-4(3H)-pyrimidinone with tert-butyl hydroperoxide at equimolar ratio of the reactants leading to selective oxidation of nitroso group to a nitro one. The product is a crystalline substance, soluble in aromatic hydrocarbons, resistant to air oxygen and moisture. The compound has been characterized by IR and 1H NMR spectroscopy and X-ray diffraction analysis. The IR spectrum of 1 contains absorption bands at 3290 (NH2, st), 2855 (S–CH2, st), 1684 (C=O, st) and 1595 (NO2, st) cm–1. In the 1H NMR spectrum of 1 there are singlets of SCH2 protons at 3.87 ppm and С≡CH at 3.12 ppm. Downfield, there are singlets of NH2 group protons at 7.77 ppm and pyrimidine ring NH protons at 10.89 ppm. According to X-ray diffraction analysis data, in the crystal there are two types of crystallographically independent molecules, geometrical parameters of which are slightly different. X-ray diffraction data show that the crystal cell contains molecules of the used solvent, dimethylformamide. The planes of the nitro and thio groups are parallel to the plane of the heterocyclic fragment. C–NO2 and C–NH2 bond lengths are 1.452(2) and 1.317(2) Å, which is usual for compounds of these classes. The CAr–S distance is 1.748(2) Å. The structural arrangement of molecules in a crystal is due to O•••H hydrogen bonding (1.91(2)–2.70(1) Å) and intermolecular N•••O interactions (2.767(3)–2.984(3) Å). Also, there are face-to-face stacking interactions, the distances between centroids of aromatic rings are 4.13–4.46 Å.

Author Biographies

E. V. Artem’eva, South Ural State University

старший преподаватель кафедры теоретической и прикладной химии

K. Yu. Petrova, South Ural State University

кандидат химических наук, старший преподаватель кафедры теоретической и прикладной химии

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