2-(2-Aryl-2-Oxoethyl)-4h-Benzo-1,4-Thiazin-3-Ones AS PRODUCTS OF THE REACTION OF 2-Aminothiophenol WITH Β-Aroylacrylic ACIDS

Beryozkina, Tetyana; Kolos, N. N.; Orlov, V. D.; Zubatyuk, Roman I.; Шишкин, Олег В.

doi:10.1080/10426500490475166

Cited by 12 publications

(10 citation statements)

References 6 publications

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“…For the synthesis and antimicrobial activity of benzimidazole derivatives, see: Gü ven et al (2007): Nofal et al (2002). For related structures, see: Beryozkina et al (2004): Kumaradhas & Nirmala (1997): Zhang et al (2008). For graph-set notation, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

“…The crystal structures of (II) i.e., 2-(2-(4-bromophenyl)-2-oxoethyl)-4H-benzo-1,4-thiazin-3-one (Beryozkina et al, 2004), (III) 2-(4-chlorobenzoylmethyl)-2H-1,4-benzothiazin-3(4H)-one (Zhang et al, 2008) and (IV) (±)-2-(hydroxy(4methoxyphenyl)methyl)-2H-1,4-benzothiazin-3(4H)-one monohydrate (Kumaradhas & Nirmala et al, 1997) have been published which are related to title compound (I), (Fig. 1).…”

Section: Crystal Datamentioning

confidence: 99%

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2-Benzoyl-2H-1,4-benzothiazin-3(4H)-one

et al. 2010

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In the title compound, C15H11NO2S, the dihedral angle between the aromatic rings is 80.35 (7)°. The heterocyclic six-membered ring is not planar: the puckering parameters of this ring are Q = 0.5308 (15) Å, θ = 63.11 (18) and ϕ = 23.5 (2)°. The molecules are linked into inversion dimers with R 2 2(8) ring motifs by pairs of N—H⋯O hydrogen bonds. The dimers are interlinked into polymeric sheets extending parallel to the bc plane by C—H⋯O hydrogen bonds, generating R 2 1(7) ring motifs. π–π interactions occur between the benzoyl phenyl rings with centroid–centroid separations of 3.9187 (15) Å.

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Section: Related Literaturementioning

confidence: 99%

Section: Crystal Datamentioning

confidence: 99%

2-Benzoyl-2H-1,4-benzothiazin-3(4H)-one

et al. 2010

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“…For microwave-assisted syntheses of related compounds, see: Dandia et al (2002). For further related literature, see: Pant & Chugh (1989); Kirchner & Alexander (1959); Beryozkina et al (2004); Pant et al (1987).…”

Section: Related Literaturementioning

confidence: 99%

“…In continuation of our ongoing studies on the synthesis of 4-aryl-2-carboxy-2,3-dihydro-1,5-benzothiazepines for various biological activities, we reacted 2-aminothiophenol with β-aroylacrylic acids, but the formation of a seven-membered ring did not occur. Several authors have reported about the 4-aryl-2-carboxy-2,3-dihydro-1,5-benzothiazepine structure for the products of the reaction of 2-aminothiophenol with βaroylacrylic acids (Pant & Chugh, 1989;Dandia et al, 2002), and others proposed the formation of 1,4-benzothiazin-3ones (Kirchner & Alexander, 1959;Beryozkina et al, 2004).…”

Section: S1 Commentmentioning

confidence: 99%

2-(4-Chlorobenzoylmethyl)-2H-1,4-benzothiazin-3(4H)-one

Zhang

Wang

et al. 2008

Acta Cryst E

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Reactions of 3-aroylacrylates with α-aminoazoles*

Kolos

Kovalenko

Borovskoy

2011

Chem Heterocycl Comp

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3-Aroylacrylic acids and their functionalized derivatives are convenient bielectrophilic reagents for the synthesis of six-membered heterocycles [1][2][3][4][5]. The formal [4+2], [3+3] or [2+4] cycloaddition schemes correspond to interaction of these compounds with 1,4-, 1,3-or 1,2-binucleophiles respectively. Reactions of 3-aroylacrylic acids with -aminoazoles remain the least studied, few publications being concerned with this problem [6,7]. However, a convenient method for the synthesis of the azolopyridine or azolopyrimidine systems is the reaction of chalcone type enone systems with -aminoazoles [8]. The synthetic availability of 3-aroylacrylic acids [9, 10], the high reactivity of an activated ethylene bond [11][12][13], and the possibility of functionalization of the carboxyl group point to the evident advantages of these bielectrophiles over the chalcones.In our work we have studied the cyclocondensation of the 3-aroylacrylates 1a-d with the 5-aminopyrazoles 2a,b and the 3-aroylacrylates 1d-g with 3-amino-1,2,4-triazole (3).There are literature reports of the formation of both pyrazolo[1,5-a]pyrimidines [14-17] and pyrazolo [3,4-b]pyridines [18][19][20] in the reaction of 5-aminopyrazoles with compounds having enone structural fragments. The use of 3-aroylacrylic acid derivatives in similar reactions permits the synthesis of functionalized dihydroazoloazine systems [6].Treatment of the esters 1a-d with 5-aminopyrazole 2a in ethanol gives high yields of the pyrazolo-[3,4-b]pyridines 4a-d as yellow crystals. The formation of the pyrazolopyridine bicycle is associated above all with the nucleophilic centers of the 5-aminopyrazole molecule [18,19]. The synthesis of pyrazolopyridines 4a-d involves the formation of an α-adduct at the pyrazole 2a C-4 atom.

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2-(2-Aryl-2-Oxoethyl)-4h-Benzo-1,4-Thiazin-3-Ones AS PRODUCTS OF THE REACTION OF 2-Aminothiophenol WITH Β-Aroylacrylic ACIDS

Cited by 12 publications

References 6 publications

2-Benzoyl-2H-1,4-benzothiazin-3(4H)-one

2-Benzoyl-2H-1,4-benzothiazin-3(4H)-one

2-(4-Chlorobenzoylmethyl)-2H-1,4-benzothiazin-3(4H)-one

Reactions of 3-aroylacrylates with α-aminoazoles*

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