Facile One‐Pot Synthesis of 4‐Hydroxy‐2‐methyl‐(2H)‐1,2‐benzothiazine‐3‐sulfonic Acid 1,1‐Dioxide

Siddiqui, Waseeq Ahmad; Ahmad, Saeed; Khan, Islam Ullah; Siddiqui, Hamid Latif; Weaver, George W.

doi:10.1080/00397910601131437

Cited by 41 publications

(48 citation statements)

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“…The derivatives of 1,2-benzothiazine exhibit a wide range of biological activities, e.g., anti inflammatory (Lombardino & Wiseman, 1972), analgesic (Gupta et al, 2002), anti cancer (Gupta et al, 1993) and anti bacterial (Zia-ur-Rehman et al, 2006), etc. In continuation of our research on the synthesis of biologically active benzothiazine derivatives (Siddiqui et al, 2007;Ahmad et al, 2010), we herein report the synthesis and crystal structure of the title compound.…”

Section: Methodsmentioning

confidence: 99%

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3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione

et al. 2012

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Key indicators: single-crystal X-ray study; T = 173 K; mean (C-C) = 0.005 Å; R factor = 0.068; wR factor = 0.133; data-to-parameter ratio = 15.6.In the title molecule, C 24 H 19 NO 6 S, the heterocyclic thiazine ring adopts a half-chair conformation with the S and N atoms displaced by 0.180 (5) and 0.497 (5) Å , respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The benzene rings of the benzothiazine unit and the methoxyphenyl group are almost coplanar, with the dihedral angle between the mean planes of these rings being 5.9 (2) , while the benzene ring of the 2-oxo-2-phenylethyl group is inclined at 79.68 (11) and 81.01 (10) , respectively, to these rings. The molecular structure is consolidated by intramolecular O-HÁ Á ÁO and C-HÁ Á ÁN interactions, and the crystal packing is stabilized by weak C-HÁ Á ÁO hydrogen bonds. Related literature

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Section: Methodsmentioning

confidence: 99%

“…For background information on the synthesis of related compounds, see: Siddiqui et al (2007). For the biological activity of 1,2-benzothiazine derivatives, see : Lombardino & Wiseman (1972); Gupta et al (1993Gupta et al ( , 2002; Zia-ur-Rehman et al (2006); Ahmad et al (2010).…”

Section: Related Literaturementioning

confidence: 99%

3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione

et al. 2012

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“…For background information on the synthesis of related compounds, see: Siddiqui et al (2007). For the biological activity of benzothiazine derivatives, see: Turck et al (1995); Zia-ur-Rehman et al (2006); Ahmad et al (2010).…”

Section: Related Literaturementioning

confidence: 99%

“…A few benzothiazines have also been studied as precursors for azodisperse dyes for polyesters (Rajagopal & Seshadri 1990). In continuation of our research on the synthesis of biologically active benzothiazine derivatives (Siddiqui et al, 2007;Ahmad et al, 2010), we herein report the synthesis and crystal structure of the title compound. …”

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confidence: 99%

1-(4-Chlorophenyl)-2-[4-hydroxy-3-(3-methoxybenzoyl)-1,1-dioxo-2H-1λ⁶,2-benzothiazin-2-yl]ethanone

et al. 2012

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Key indicators: single-crystal X-ray study; T = 123 K; mean (C-C) = 0.004 Å; R factor = 0.054; wR factor = 0.111; data-to-parameter ratio = 15.8.In the title molecule, C 24 H 18 ClNO 6 S, the heterocyclic thiazine ring adopts a half-chair conformation with the S and N atoms displaced by 0.406 (5) and 0.444 (5) Å , respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The methoxybenzoyl and the chlorophenyl rings lie roughly parallel to each other, with a dihedral angle between the mean planes of these rings of 8.86 (10) . The molecular structure is consolidated by intramolecular O-HÁ Á ÁO and C-HÁ Á ÁO interactions and the crystal packing is stabilized by intermolecular O-HÁ Á ÁO and C-HÁ Á ÁCl hydrogen bonds. Table 1 Hydrogen-bond geometry (Å , ). etc. A few benzothiazines have also been studied as precursors for azodisperse dyes for polyesters (Rajagopal & Seshadri 1990). In continuation of our research on the synthesis of biologically active benzothiazine derivatives (Siddiqui et al., 2007;Ahmad et al., 2010), we herein report the synthesis and crystal structure of the title compound. Related literatureThe bond distances and angles in the title compound ( Fig. 1) agree very well with the corresponding bond distances and angles reported in closely related compounds (Siddiqui et al., 2008). The heterocyclic thiazine ring adopts a half chair conformation with the S1 and N1 atoms displaced by 0.406 (5) and 0.444 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The methoxybenzoyl and the chlorophenyl rings lie roughly parallel to each other with a dihedral angle between the mean planes of these rings of 8.86 (10)°; the distance between the centroids of these rings is 3.828 (14) Å. The molecular structure of the title compound is consolidated by intramolecular interactions O3-H3O···O4 and C24-H24···O2 and the crystal packing is stabilized by intermolecular O3-H3O···O4 and C3-H3···Cl1 hydrogen bonds ( Fig. 2 and Table 1). S2. ExperimentalA mixture of (4-hydroxy-1,1-dioxido-2H-1,2-benzothiazin-3-yl)(3-methoxyphenyl) methanone (5.0 g, 0.015 mol), K 2 CO 3 (2.07 g, 0.015 mol) and 4-chlorophenacyl bromide (3.50 g, 0.015 mol) in acetonitrile (30 ml) was refluxed for 3 h. The contents of the flask were poured on ice cold HCl (5%, 30 ml). The precipitate of the title compound thus formed was

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“…3 Thus, it was proposed to prepare new drug candidates through the Ritter reaction, by analogy to the work of Buc,4 condensing N-(hydroxymethyl)-saccharin with nitriles. (2), prepared in 92% yield from saccharin (1) and formaldehyde, 5 was reacted with equimolar amount of diverse nitriles in H 2 SO 4 at room temperature to afford, after work-up, the new crystalline amides (3) …”

Section: 2mentioning

confidence: 99%

Ritter reaction of N-(hydroxymethyl)saccharin with nitriles: synthesis of new N-(amidomethyl)saccharins

Mattos

2013

Proceedings of the 15th Brazilian Meeting on Organic Synthesis Proceedings

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Facile One‐Pot Synthesis of 4‐Hydroxy‐2‐methyl‐(2H)‐1,2‐benzothiazine‐3‐sulfonic Acid 1,1‐Dioxide

Cited by 41 publications

References 8 publications

3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione

3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione

1-(4-Chlorophenyl)-2-[4-hydroxy-3-(3-methoxybenzoyl)-1,1-dioxo-2H-1λ⁶,2-benzothiazin-2-yl]ethanone

Ritter reaction of N-(hydroxymethyl)saccharin with nitriles: synthesis of new N-(amidomethyl)saccharins

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Facile One‐Pot Synthesis of 4‐Hydroxy‐2‐methyl‐(2H)‐1,2‐benzothiazine‐3‐sulfonic Acid 1,1‐Dioxide

Cited by 41 publications

References 8 publications

3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ6,2-benzothiazine-1,1,4-trione

3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ6,2-benzothiazine-1,1,4-trione

1-(4-Chlorophenyl)-2-[4-hydroxy-3-(3-methoxybenzoyl)-1,1-dioxo-2H-1λ6,2-benzothiazin-2-yl]ethanone

Ritter reaction of N-(hydroxymethyl)saccharin with nitriles: synthesis of new N-(amidomethyl)saccharins

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3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione

3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione

1-(4-Chlorophenyl)-2-[4-hydroxy-3-(3-methoxybenzoyl)-1,1-dioxo-2H-1λ⁶,2-benzothiazin-2-yl]ethanone