4-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-2H-1,4-benzothiazin-3(4H)-one

Abstract

In the title compound, C18H16N4OS, the six-membered heterocycle of the benzo­thia­zine fragment exhibits a screw-boat conformation. The dihedral angles between the plane through the triazole ring and those through the fused and terminal benzene rings are 76.68 (11) and 71.0 (1)°, respectively; the benzene rings are nearly perpendicular [dihedral angle = 79.6 (1)°]. In the crystal, mol­ecules are linked by C—H⋯N and C—H⋯O inter­actions, forming a three-dimensional network.

4-[(1-Benzyl-1,2,3-triazol-5-yl)methyl]-2H-1,4-benzothiazin-3(4H)-one

“…With respect to biological applications, these derivatives have been found to be potent antiinflammatories (Chia et al, 2008), anti-microbials (Barazarte et al, 2008), herbicidals (Takemoto et al, 1994 and fungicidals (Yaltirik et al, 2001). The present work is a continuation of the investigation of the benzothiazine derivatives published recently by our team, including the isomer of the present compound (Sebbar et al, 2014).…”

“…For the biological activity and pharmaceutical properties of benzothiazines and their derivatives, see: Chia et al (2008); Barazarte et al (2008); Takemoto et al (1994); Yaltirik et al (2001). For a related structure, see: Sebbar et al (2014). For ring puckering parameters, see: Cremer & Pople (1975).…”

4-(Prop-2-ynyl)-2H-1,4-benzothiazin-3(4H)-one

“…For general background to the synthesis of 1,4-benzothiazines derivatives, see: Sebbar et al (2014); Zerzouf et al (2001). For the pharmacological activity of 1,4-benzothiazine derivatives, see: Trapani et al (1985); Yaltirik et al (2001); Wammack et al (2002).…”

“…E70, o641 (Trapani et al, 1985) and analgesic (Wammack et al, 2002;Yaltirik et al, 2001) drugs. In our previous work we have reported the synthesis of new 1,4-benzothiazine derivatives for biological activities (Zerzouf et al, 2001;Sebbar et al, 2014). The reactivity of propargyl bromide towards 3-oxo-1,4-benzothiazine under phase-transfer catalysis conditions using tetra n-butyl ammonium bromide (TBAB) as catalyst and potassium carbonate as base, leads to the formation of the title compound in good yields.…”

(2Z)-2-Benzylidene-4-n-butyl-3,4-dihydro-2H-1,4-benzothiazin-3-one

“…For the pharmaceutical and biochemical properties of benzothiazine and their derivatives, see: Malagu et al (1998); Wammack et al (2002); Rathore & Kumar (2006); Zia-ur-Rehman et al (2009). For related structures, see: Sebbar et al (2014); Saeed et al (2010). For puckering calculations, see: Cremer & Pople (1975).…”