Syntheses and Crystal Structures of 4-Amino-3-(3-hydroxypropyl)-1H-1,2,4-triazole-5(4H)-thione and 6-(4-Biphenylyl)-3-(3-hydroxypropyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine

Starting with y-butyrolactone, 4-amino-3-（3-hydroxypropyl）-1H-1,2,4-triazole-5-（4H） thione 1 was prepared, and cyclization of it with 4-phenylbromoacetophenone gave 6-（4-biphenylyl）- 3-（3-hydroxypropyl）-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine Ⅱ. The structures of Ⅰ and Ⅱ were determined by elemental analyses, IR, ^1H NMR, ^13C NMR, and X-ray diffraction. Crystal data for 1： C5H10N4OS, Mr = 174.23, monoclinic system, space group P21/c, a =8.4568（6）, b = 22.8905（16）, c = 9.2625（6） A, β= 114.172（1）°, V= 1635.82（19） A^3, F（000） = 736, Z= 8, Dc = 1.415 g/cm^3, 2 λ=0.71073 A,μ = 0.346 mm^-1 and the final R = 0.0603 for 2870 unique reflections with 1993 observed ones （I 〉 2σ（I）. Crystal data for Ⅱ： C19H18N4OS, Mr = 350.43, monoclinic system, space group P21/c, a = 6.7481（7）, b = 8.2647（8）, c = 30.075（3） A, β= 94.445（2）°, V= 1672.3（3） A3, F（000） = 736, Z = 4, Dc = 1.392 g/cm^3, λ=0.71073 A,μ= 0.209 mm^-1 and the final R = 0.0667 for 3000 unique reflections with 2534 observed ones （I 〉 2σ（I））. In the crystal of compound Ⅱ, the five-membered triazole ring and two benzene rings are coplanar, while the six-membered thiadiazine ring is slightly distorted, with an r.m.s deviation of 0.227（1） A. Some hydrogen bonding interactions are observed and π-π stacking interactions between adjacent molecules are found in the packing diagrams of the two compounds.

Synthesis and Crystal Structure of 3-(2-Hydroxybenzly)-4-(4-Hydroxybenzylideneamino)-(1H) -1,2,4-Triazole-5-Thione and Its Antibacterial Activities

The title compound C15H12N4O2S was synthesized by the reaction of 3-（2-hydroxybenzyl）-4-amino-（1H）-1,2,4-triazole-5-thione with 4-hydroxybenzaldehyde in ethanol and characterized by IR, ^1H NMR spectra and elemental analysis. Its structure has been determined by X-ray diffraction analysis. The crystal belongs to monoclinic, space group C2/c with a = 27.990（3）, b = 13.1326（14）, c = 7.9770（8） A, β= 105.787（2）°, V = 2821.6（5）A^3, Z = 8, Mr= 312.35,μ= 0.243 mm^-1, Dc = 1.471 g/cm^3 and F（000） = 1296. The structure was solved by direct methods.and refined to a Rint value of 0.0388. The crystal structure involving in intermolecular N-H…S and O-H…S hydrogen bonds is observed, meanwhile intramolecular O-H…N hydrogen bond is also found. Their biological activities have been measured. The results show that this type of compound has certain antibacterial activity for Staphylococous aureus and Bacillus subtilis.

Synthesis and Crystal Structure of 4-Salicyli deneamino-3-methyl-1,2,4-triazol-5-thione

The crystal structure of 4-salicylideneamino-3-methyl-1,2,4-triazol-5-thione 1 (C10H10N4OS, Mr = 234.28) has been determined by single-crystal X-ray diffraction method. The crystal belongs to monoclinic, space group P21/n with a = 12.697(3), b = 7.4072(15), c = 12.750(3) , b = 117.68(3), V = 1061.85(4) 3, Z = 4, Dc = 1.465 g/cm3, m = 0.288 mm-1 and F(000) = 488. R = 0.0584 and wR = 0.1642 for 2660 unique reflections with 2130 observed ones (I > 2s(I)). The results confirmed that the configuration of the title compound at the azomethine C=N bond is E and 1 can be assigned as the thione tautomeric form. All atoms of the title compound are essentially coplanar.

Synthesis and Crystal Structure of 5-Nitro-4-salicylidene-amino-3-methyl-1,2,4-triazol-5-thione

The crystal structure of 5-nitro-4-salicylideneamino-3-methyl-1,2,4-triazole-5-thione ([C 10 H 9N 5O 3S]·HCON(CH 3) 2, M r=352.38)(CCDC No. 216094) was determined by the single crystal X-ray diffraction method. The crystal belongs to a triclinic system, the space group is P1 with unit cell constants a= 0.6113(2) nm, b=1.0836(4) nm, c=1.3132(5) nm, α=74.523(7)°, β=117.68(3)°, γ= 79.769(7)°, V=0.8245(5) nm 3, Z=2, D c=1.419 g/cm 3, μ=0.228 mm -1 , F(000)=368, R and wR are 0.0579 and 0.1040, respectively, beasd on 3348 unique reflections of which 1925 reflections were observed[I>2σ(I)]. The results indicate that the title compound can be assigned to the thione tautomeric form rather than the thiol tautomeric form. It contains a five membered triazole ring and a phenyl ring with a dihedral angle of 4.35°. The intermolecular hydrogen bond N3_H3…S1, O1_H1…O4 can be observed.

Synthesis of N-Aryl-2-(1′,6′-dihydro-6′-pyridazinone-3′-carbonyl) Thiosemicarbazides and Their Related Heterocyclic Compounds

Dihydro-3-hydrozinocarbonyl-6-pyridazinone(compound 2) were prepared from α-ketoglutaric acid and hydrazine hydrate. A series of N-aryl-2-(1′,6′-dihydro-6′-pyridazinone-3′-carbonyl) thiosemicarbazides 3a_3f were synthesized from the reaction of aryl isothiocyanates with compound 2. The terminal compounds 1,3,4-thiadiazole, 1,3,4-oxadiazole and 1,2,4-triazol-5-thione derivatives were cyclized from compounds 3a_3f. Their structures were confirmed by IR, 1H NMR, MS and elemental analyses.