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

摘要

Starting with γ-butyrolactone, 4-amino-3-(3-hydroxypropyl)-1H-1,2,4-triazole-5-(4H) thione Ⅰ 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, ~(13)C NMR, and X-ray diffraction. Crystal data for Ⅰ: C_5H_(10)N_4OS, M_r = 174.23, monoclinic system, space group P2_1/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, D_c = 1.415 g/cm~3, 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: C_(19)H_(18)N_4OS, M_r = 350.43, monoclinic system, space group P2_1/c, a = 6.7481(7), b = 8.2647(8), c = 30.075(3) A, β = 94.445(2)°, V = 1672.3(3) A~3, F(000) = 736, Z = 4, D_c = 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.