Synthesis of novel N-alkyl-2-(3,5-dimethyl-1,1-dioxido-2H-1,2,6-thiadiazin-4-yl)benzamides as potential antimicrobial agents

Bhatt, Nilay; Vyas, K. B.; Nimavat, K. S.; Govender, Thavendran; Kruger, Hendrik G.; Maguire, Glenn E. M.; Bhatt, Praghnesh

doi:10.1016/j.jopr.2013.03.008

Cited by 5 publications

(4 citation statements)

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“…We previously have reported the 3,5-dimethyl based structure with an aromatic ring at position 4ofthe thiadiazine ring containing an ethyl ester function [2].Wehave reported the synthesis of N-alkyl analogues of 1,2,6-thiadiazine-1,1-dioxides as potential antimicrobialagents [3]. Herein we report the crystal structure of a N-butyl analogues from thesameclass of 1,2,6-thiadiazine-1,1-dioxides.…”

Section: Discussionmentioning

confidence: 95%

Crystal structure of N-butyl-2-(3,5-dimethyl-1,1-dioxido-2H-1,2,6- thiadiazin-4-yl)benzamide, C16H21N3O3S

Bhatt

Govender

et al. 2014

Zeitschrift Für Kristallographie - New Crystal Structures

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C 16 H 21 N 3 O 3 S, monoclinic, P2 1 /n (no. 14), a =7.7608(2) Å, b =15.3483(4) Å, c =13.6538(3) Å, b =94.283(2)°,Source of material 2-(3,5-dimethyl-1,1-dioxido-2H-1,2,6-thiadiazin-4-yl)benzoic acid (0.017 mol) and carbonyldiimidazole (0.017 mol) in dry tetrahydrofuran (50 ml) was stirred for 30 mins at room temperature. To this solution N-butyl amine (0.021 mol) was slowly added and the contents stirred for 12 hrs at room temperature until thereactionwas completed(TLCR f =0.8 using 80% ethyl acetate/hexane). The solvent was then completely evaporated and the residual mass was treated with 5% HCl (25 ml) and stirred for 1hr.The pale yellow product was filtered giving a6 5% yield. m.p. =466 K. Crystals suitalble for X-ray analysis were grown in methanol/ethylacetate at room temperature. Experimental detailsAllhydrogenatoms,except H1 and H3, were placed in idealised positions and refined in riding models with U iso assigned the values to be 1.2 or 1.5 times U eq of the atomst ow hich they are attached and the constraint distancesofC-H ranging from 0.95 Å to 0.99 Å. The hydrogens H1 and H3 were located in the difference electron density maps and refined independently DiscussionThe synthesis of 1,2,6-thiadiazine-1,1-dioxides derivatives was first reported using sulfamide with alpha and beta diketones [1]. We previously have reported the 3,5-dimethyl based structure with an aromatic ring at position 4ofthe thiadiazine ring containing an ethyl ester function [2].Wehave reported the synthesis of N-alkyl analogues of 1,2,6-thiadiazine-1,1-dioxides as potential antimicrobialagents [3]. Herein we report the crystal structure of a N-butyl analogues from thesameclass of 1,2,6-thiadiazine-1,1-dioxides. The sulfur atom deviates from the plane of the ring by 0.105 Å. There is ac lassic hydrogen bond for N1×××O3' = 2.8134(16) Åand N3×××O2'' =2.9624(16) Å.These connections create a2-dimensional, hydrogen bonded network.

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Section: Discussionmentioning

confidence: 95%

Crystal structure of N-butyl-2-(3,5-dimethyl-1,1-dioxido-2H-1,2,6- thiadiazin-4-yl)benzamide, C16H21N3O3S

Bhatt

Govender

et al. 2014

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The2 -(2,4-dioxopentan-3-yl)benzoica cid are precursors for a broader family of 1,2,6-thiadiazine-1,1-dioxides [2,3].Here we report the synthesis and structure of 2-(2,4-dioxopentan-3-yl)-benzoic acid (figure). In the crystal intermolecular hydrogen bonding originating from carboxy groups of neighboring molecules(O×××O=2.6340(12) Å) create dimers.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-(2,4-dioxopentan-3-yl)benzoic acid, C12H12O4

Bhatt

Govender

et al. 2014

Zeitschrift Für Kristallographie - New Crystal Structures

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C 12 H 12 O 4 ,monoclinic, P2 1 /n (no. 14), a =8.9609(6) Å, b =8.6155(5) Å, c =14.3356(9) Å, b =100.422(1)°,Source of material 2-bromobenzoic acid (25g,0.12mol)and copper iodide 1.0g (4% w/w)inacetylacetone (50 ml) was stirred vigorously for 1hr at room temperature. To this solution sodium hydride (12.43 g, 0.31 mol, 60% in paraffin oil) was added slowly and the temperature raised to 50-55°C for 1hr. Thetemperature of the reaction mixture was then further increased to 80-85°C and maintained for 5hrs. After cooling, the reaction mixture was quenched in water(500ml). Theexcess acetyl acetone was removed by extraction usingdiethylether (2´250ml). The aqueous layer was then acidified using aconcentrated hydrochloricacid solution to get an oily residue, which slowly crystallized as alight brown coloured solid, yield =6 2%, m.p. =4 14-415 K. Recrystallization from methanol at room temperature afforded colourless crystals suitable forX-ray analysis. Experimental detailsAllnon-hydrogen atoms were refined anisotropically. All hydrogen atoms, except H2 and H4, were placed in idealised positions and refined in riding models with U iso assigned the values to be 1.2 or 1.5 times those of their parent atomsand the constraint distances of C-H ranging from 0.95 Åto0.98 Å.

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“…Some2 -(2,4-dioxopentan-3-yl)benzoic acid derivatives have been synthesised from arange of arylhalides and acetylacetone [1].W eh ave employed these compounds as precursors for the synthesis of 1,2,6-thiadiazine-1,1-dioxides [2,3].I nt his paper we report the synthesis and the X-ray structure of the methyl ester of 2-(2,4-dioxopentan-3-yl)benzoic acid ( Fig.). Thee ster compound shows no hydrogen bonding or p interactions in the crystal structure.…”

Section: Discussionmentioning

confidence: 99%