Syntheses of 2,4‐diaryl‐2,3‐dihydro‐1,5‐benzothiazepines

Katritzky, Alan R.; Rogovoy, Boris V.; Chassaing, Christophe; Vvedensky, Vladimir Y.; Forood, Behrouz; Flatt, Brenton; Nakai, Hisao

doi:10.1002/jhet.5570370642

Cited by 23 publications

(17 citation statements)

References 11 publications

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“…at δ 3.56 (dd, J = 6.9 Hz, J = 17.6 Hz, 1H; CO-CH2-CH-S), δ 3.64 (dd, J = 7.3 Hz, J = 17.5 Hz, 1H; CO-CH2-CH-S), δ 4.74 (t, J = 6.7 Hz, 1H; CO-CH2-CH-S) and a carbonyl group in 13 C NMR spectrum at δ 197.15 which is in agreement with the reported data for a Michael adduct [31]. The IR spectra of this compound indicated the presence of NH2 at 3352 cm -1 .…”

Section: Resultssupporting

confidence: 81%

Di-cationic Ionic Liquid Catalyzed Synthesis of 1,5-Benzothiazepines

Sakirolla¹,

Tadiparthi²,

Yaeghoobi³

et al. 2017

Asian J. Chem.

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A simple and elegant method for the synthesis of 1,5-benzothiazepines has been developed using di-cationic liquid as a solvent cum catalyst by the reaction of o-aminothiophenol with a variety of chalcones under mild reaction conditions. Furthermore the reusability of the catalyst has also been studied for three cycles. All the reactions are proposed to proceed through a 1,4-conjugate Michael addition followed by a cyclo-condensation reaction. [21][22][23]. In addition to this, the special properties of the ionic liquids have influenced the rate of chemical reactions such as elimination reactions where, the rate of the reaction in ionic liquids was observed to be faster than those carried out in conventional organic solvents [24]. Notably, multifunctional group dicationic ionic liquids have been reported to have a greater range of physical properties than traditional and singly charged ionic liquids. They are often more thermally stable, less volatility and are more flexible in tuning their physicochemical virtues [25,26]. Herein, we report an efficient synthesis of various 1,5-benzothiazepines using dicationic liquids as a catalyst and as well as solvent. EXPERIMENTALGeneral procedure: A mixture of o-aminothiophenol (1.2 mmol)/o-phenylenediamine (1 mmol), chalcone (1.0 mmol) and IL-C (0.2 mmol, 0.1 g per mmol of chalcone) was stirred at 80 °C for 80 min under nitrogen atmosphere. After completion of the reaction, which was monitored by TLC, the reaction mixture was diluted with water (10 mL) and extracted with diethyl ether (3 × 25 mL). The combined organic layer was separated and dried over anhydrous magnesium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by crystallization in ethanol to afford the pure solid 1,5-benzothiazepines. The water present in the aqueous layer was subjected for distillation and the left over residue contains the pure ionic liquid, which could be recycled.

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Section: Resultssupporting

confidence: 81%

Di-cationic Ionic Liquid Catalyzed Synthesis of 1,5-Benzothiazepines

Sakirolla¹,

Tadiparthi²,

Yaeghoobi³

et al. 2017

Asian J. Chem.

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“…[3] The latter are well-known starting materials in the preparation of 1,5-benzothiadiazepines with anti-anginal and anti-hypertensive activities. [33] In this context one can believe that these fluorinated derivatives (from this work and refs.…”

Section: Discussionmentioning

confidence: 95%

Fluorinated 1,3λ⁴δ²,2,4‐Benzodithiadiazines − A Synthetic, Structural and Theoretical Study

et al. 2002

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The series of title compounds has been prepared through both electrophilic (C6HnF5−n−N=S=N−SiMe3 + SCl2) and nucleophilic (C6HF4−S−N=S=N−SiMe3 + CsF) intramolecular ortho‐cyclisation reactions, and the former route seems to be the more effective. High regioselectivity of the ring‐closing procedures is observed in both cases. The compounds were characterised by X‐ray crystallography and multinuclear (1H, 13C, 15N and 19F) NMR spectroscopy. In accordance with GIAO calculations, 15N{1H} experiments and the effects observed on complete substitution of hydrogen by fluorine, the high‐field signal in the 15N NMR spectra can be assigned to N‐4 and the low‐field signal to N‐2. In the crystal, 5,6,7‐trifluoro‐ (5) and 5,6,8‐trifluoro‐1,3λ4δ2,2,4‐benzodithiadiazine (6) are planar, whereas the 6,8‐difluoro derivative 3 is bent along the S1···N4 line by 8.3°. According to NICS calculations the heterocycle moiety in this compound class is antiaromatic while the carbocycle is aromatic. The fluorine substituents increase the aromaticity − and in some cases (especially when a fluorine atom is present in the 8‐position) the antiaromaticity − of the corresponding rings. The ortho‐fluoro‐containing starting material C6HnF5−n−N=S=N−SiMe3 (n = 2: 10) cyclises to the fluorinated 2,1,3‐benzothiadiazole 27 upon treatment with CsF instead of SCl2. For starting compound 6‐HC6F4−S−N=S=N−SiMe3 (14) the planar (Z,E) configuration features a short intramolecular H···N contact, as evidenced by X‐ray diffraction. Both the reaction pathways mentioned are also discussed. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2003)

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“…24 To a mechanically-stirred solution of 2-amino-6-chlorobenzothiazole (4g, 21.7 mmol, 1.0 equiv) in 84% aq. phosphoric acid (80 mL) was added a solution of sodium nitrite (9.0 g, 13 mmol, 6.0 equiv) in water (28 mL) dropwise below the surface at -10 .…”

Section: Experimental Procedures For the Synthesis Of Thiazolesmentioning

confidence: 99%

Dual C–H activations of electron-deficient heteroarenes: palladium-catalyzed oxidative cross coupling of thiazoles with azine N-oxides

Xuan

Liu

et al. 2013

Tetrahedron

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Syntheses of 2,4‐diaryl‐2,3‐dihydro‐1,5‐benzothiazepines

Cited by 23 publications

References 11 publications

Di-cationic Ionic Liquid Catalyzed Synthesis of 1,5-Benzothiazepines

Di-cationic Ionic Liquid Catalyzed Synthesis of 1,5-Benzothiazepines

Fluorinated 1,3λ⁴δ²,2,4‐Benzodithiadiazines − A Synthetic, Structural and Theoretical Study

Dual C–H activations of electron-deficient heteroarenes: palladium-catalyzed oxidative cross coupling of thiazoles with azine N-oxides

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Syntheses of 2,4‐diaryl‐2,3‐dihydro‐1,5‐benzothiazepines

Cited by 23 publications

References 11 publications

Di-cationic Ionic Liquid Catalyzed Synthesis of 1,5-Benzothiazepines

Di-cationic Ionic Liquid Catalyzed Synthesis of 1,5-Benzothiazepines

Fluorinated 1,3λ4δ2,2,4‐Benzodithiadiazines − A Synthetic, Structural and Theoretical Study

Dual C–H activations of electron-deficient heteroarenes: palladium-catalyzed oxidative cross coupling of thiazoles with azine N-oxides

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Product

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Fluorinated 1,3λ⁴δ²,2,4‐Benzodithiadiazines − A Synthetic, Structural and Theoretical Study