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Novel method for synthesizing phenothiazine compounds

A technology of phenothiazines and compounds, which is applied in the field of synthesizing phenothiazines, can solve the problems of synthesizing phenothiazines that have not been reported, and achieve the effects of low solvent toxicity, simple operation and broad application prospects

Active Publication Date: 2015-04-22
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there is no report on the synthesis of phenothiazine compounds using benzothiazole and its derivatives and o-iodobromobenzene and its derivatives as raw materials

Method used

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  • Novel method for synthesizing phenothiazine compounds
  • Novel method for synthesizing phenothiazine compounds
  • Novel method for synthesizing phenothiazine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the synthesis of phenothiazine

[0025]

[0026] 135mg (1mmol) benzothiazole, 566mg (2mmol) o-bromoiodobenzene, 25mg (0.1mmol) CuSO 4 ·5H 2 O, 14 mg (0.1 mmol) Ligand L1, 138 mg (1 mmol) K 2 CO 3 , 2g PEG-400, added to a 10mL reaction tube, sealed, and reacted at 50°C for 20h. After the reaction stopped, it was extracted with ethyl acetate, washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure, separated and purified by silica gel column chromatography to obtain 160 mg of phenothiazine with a yield of 80%.

[0027] MS (EI + ):m / z:199(M + ,100),167(M-S,65); 1 H NMR (400MHz, DMSO-d 6 )δ8.61(s,1H,NH),6.99(td,J=7.6,1.4Hz,2H,ArH),6.94–6.88(m,2H,ArH),6.78–6.69(m,4H,ArH).

Embodiment 2

[0028] Embodiment 2: the synthesis of 2-chlorophenothiazine

[0029]

[0030]135 mg (1 mmol) benzothiazole, 158 mg (0.5 mmol) 2-bromo-4-chloro-1-iodobenzene, 16 mg (0.2 mmol) CuO, 2 mg (0.01 mmol) ligand L2, 28 mg (0.5 mmol) KOH, Add 2g of PEG-300 into a 10mL reaction tube, seal it, and react at 90°C for 3h. After the reaction stopped, it was extracted with ethyl acetate, washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, the filtrate was distilled under reduced pressure, separated and purified by silica gel column chromatography to obtain 151 mg of 2-chlorophenothiazine, the yield 65%.

[0031] MS (EI + ):m / z:198(M-Cl,100),233(M + ,78),235(M + ,25),201(M-S,25). 1 H NMR (400MHz, DMSO-d 6 )δ8.77(brs,1H,NH),7.04–6.98(m,1H,ArH),6.96–6.88(m,2H,ArH),6.82–6.75(m,2H,ArH),6.73–6.66(m ,2H,ArH).

Embodiment 3

[0032] Embodiment 3: the synthesis of 2-fluorophenothiazine

[0033]

[0034] 135 mg (1 mmol) benzothiazole, 300 mg (1.0 mmol) 2-bromo-4-fluoro-1-iodobenzene, 6.4 mg (0.1 mmol) Cu, 21.6 mg (0.1 mmol) ligand L2, 978 mg (3 mmol) Cs 2 CO 3 , 2g PEG-100, added to a 10mL reaction tube, sealed, and reacted at 110°C for 14h. After the reaction stopped, extracted with ethyl acetate, washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, the filtrate was distilled under reduced pressure, separated and purified by silica gel column chromatography to obtain 156 mg of 2-fluorophenothiazine, the yield 72%.

[0035] MS (EI + ):m / z:217(M + ,100),185(M-S,88). 1 H NMR (400MHz, DMSO-d 6 )δ8.81(s,1H,NH),7.01(td,J=7.7,1.5Hz,1H,ArH),6.97–6.89(m,2H,ArH),6.78(t,J=7.5Hz,1H, ArH), 6.70(d, J=7.9Hz, 1H, ArH), 6.59(td, J=8.5, 2.7Hz, 1H, ArH), 6.53(dd, J=10.5, 2.6Hz, 1H, ArH).

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Abstract

The invention develops a method for synthesizing phenothiazine compounds by using benzothiazole and derivatives thereof as well as 1-bromo-2-iodobenzene and derivatives thereof as raw materials and copper or copper salt / N-alkoxy-1H-pyrrolic amide system as a copper catalyst. The method is a brand-new method for synthesizing phenothiazine compounds. The method has the characteristics of low temperature, short reaction time, low solvent toxicity and wide substrate adaptability, and has wide application prospects in the aspect of preparation of medicines, pesticides and materials.

Description

technical field [0001] The present invention relates to a method of synthesizing phenothiazines with copper or copper compounds as catalysts, N-alkoxy-1H-pyrrole amides as ligands, and benzothiazole compounds and o-iodobromobenzene compounds as raw materials. compound method. Background technique [0002] Phenothiazines play an important role in the fields of medicine and materials, and have broad application prospects (a) Jaszczyszyn, A.; Gasiorowski, K.; Swiatek, P.; Malinka, W.; Cieslik-Boczula, K. ; Petrus, J.; Czarnik-Matusewicz, B. Pharmacol. Rep. 2012, 64, (1), 16-23.b) Jo, H.J.; Nam, J.E.; Kim, D.-H.; Kim, H. ; Kang, J.-K. Dyes and Pigments 2014, 102, 285-292.). [0003] The traditional method for synthesizing phenothiazine compounds mainly contains the following types: 1) the cyclization of diphenylthio compounds, which is affected by many aspects such as steric hindrance and electronic properties (Yale, H.L.J.Am.Chem.Soc .1955,77,2270-2.); 2) The cyclization of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/20
CPCC07D279/20
Inventor 万一千黄漫娜黄冬婷朱新海
Owner SUN YAT SEN UNIV
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