Two regioisomers of condensed thioheterocyclic triazine synthesized from 6-phenyl-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-5-one

Abstract

In the crystal structure of 6-phenyl-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-5-one, C(9)H(7)N(3)OS, (I), the 1,2,4-triazine moieties are connected by face-to-face contacts through two kinds of double hydrogen bonds (N-H...O and N-H...S), which form planar ribbons along the a axis. The ribbons are crosslinked through C-H...pi interactions between the phenyl rings. The molecular structures of two regioisomeric compounds, namely 6-phenyl-2,3-dihydro-7H-1,3-thiazolo[3,2-b][1,2,4]triazin-7-one, C(11)H(9)N(3)OS, (II), and 3-phenyl-6,7-dihydro-4H-1,3-thiazolo[2,3-c][1,2,4]triazin-4-one, C(11)H(9)N(3)OS, (III), which were prepared by the condensation reaction of (I) with 1,2-dibromoethane, have been characterized by X-ray crystallography and spectroscopic studies. The crystal structures of (II) and (III) both show two crystallographically independent molecules. While the two compounds are isomers, the unit-cell parameters and crystal packing are quite different and (II) has a chiral crystal structure.

Transformation of a CuII Thiazolo‐1,2,4‐triazine Derivative from a Metastable Coordination Network to a Monomer in Solution and Vapor Conditions

“…The ferromagnetic interaction of 5a also decreased with the color change. Generally, the vapochromism is mainly induced due to two reasons: (i) a coordination exchange reaction between the metal and the solvents [15][16][17][18] and (ii) a change in the crystal packing due to inclusion of solvents. [19][20][21][22][23][24][25] In this case, we suggest that a dynamic disproportionation reaction of 5a (CuCl 2 /3a = 1:1) occurred and produced a new aggregation state composed of the mononuclear complex 6a (CuCl 2 /3a = 1:2) and the solvated metal ion in the solid.…”

“…[16] The ethyl-(2b and 3b) and benzyl-substituted (2c and 3c) Scheme 1. Synthetic routes for the condensed heterocyclic rings and their complexation reactions, (x) dibromoethane, EtONa, (y) CuCl 2 ·2H 2 O, 2-propanol, (z) 2-propanol and/or water.…”

Cocrystals of 6-propyl-2-thiouracil: N—H...OversusN—H...S hydrogen bonds

“…19 entries showed R 2 2 (8) motifs characterized by two N-HÁ Á ÁO hydrogen bonds; the S atoms take part as acceptors only in five of them [refcodes LACJIJ (Tashkhodzhaev et al, 2002), XUHJIY (Pawlowski et al, 2009), XEXWAZ, XEXWED and XEXWIH (Balalaie et al, 2006)], whereby chains stabilized by N-HÁ Á ÁS hydrogen bonds are observed only in XUHJIY. Nine structures contain two different R 2 2 (8) patterns with either two N-HÁ Á ÁO or two N-HÁ Á ÁS hydrogen bonds [refcodes CASPUI (Hu et al, 2005), CUKBOA (Hori et al, 2009), GEMCAC (Read et al, 1988), PABPAL (Chierotti et al, 2010), RAPNAY (Long et al, 2005), TURCIL01 (Tiekink, 1989), TURCIL02 (Munshi & Guru Row, 2006), WIVJAM (Coxall et al, 2000) and ZEWDOU (Ferrari et al, 1995)]. Furthermore, six entries showed R 2 2 (8) interactions consisting of two N-HÁ Á ÁS hydrogen bonds [refcodes FALWOF (Orzeszko et al, 2004), JESWEK (Xue et al, 2006), MTURAC (Hawkinson, 1975), PABNIR (Chierotti et al, 2010), VOKBUT (Luo et al, 2008) and ZUWMUZ (Branch et al, 1996)].…”

CRYSTAL STRUCTURE OF 3-tert-BUTYL- PYRAZOLO[5,1-с][1,2,4]TRIAZINE-3,4-DIYL DICARBOXYLATES

“…Qualitative and quantitative structural characteristics of heterocyclic compounds are significant in studying reaction mechanisms as well as in the synthesis of novel biologically active materials [ 1 - 4 ]. It is well known that the majority of saturated six-membered heterocycles adopt the chair conformation whereas the structure of aromatic derivatives is almost planar [ 5 - 9 ]. Deviations from the planarity may arise due to a set of various steric and electronic factors [ 10 ].…”