Method for directly synthesizing 1, 3-dithioindolizine compound by using substituted 2-aryl indolizine
A technology of dithioindole azine and aryl indole azine is applied in the field of directly synthesizing 1,3-dithioindole azine compounds from substituted 2-aryl indole azine, and can solve the problem of harsh reaction conditions, The problems of low product efficiency and high price can achieve the effects of high reaction yield, good substrate universality and easy operation.
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Embodiment 1
[0016] Example 1 Synthesis of 2-phenyl-1,3-bis(p-methylphenylthio)indoxazine
[0017] Add 2-phenylindolezine (0.26 mmol, 0.050 g) and p-cresylthiol (0.54 mmol, 0.067 g), KI (10 mol%, 0.005 g), DCE (1 mL) into a 25 mL reaction flask. The reaction was stirred under an oxygen atmosphere at 60 °C until the reaction was completed, the reaction time was 7 h, and the reaction was quenched with saturated sodium thiosulfate, and then the reaction mixture was diluted with 5ml ethyl acetate and 10ml water, and diluted with 10ml ethyl acetate Extract, wash the organic layer with 10ml saturated salt brine, dry over anhydrous sodium sulfate, distill under reduced pressure, purify the crude product by silica gel chromatography, and elute with petroleum ether:ethyl acetate=300:1 to obtain 2-benzene as a white solid 1,3-bis(p-tolylthio)indoxazine 90 mg, yield 79%, melting point: 151-153 oC; 1H NMR (400MHz, CDCl3) δ 8.33 (d, J = 7.0 Hz, 1H), 7.68 (d, J = 8.8 Hz, 1H), 7.43 (dd, J= 7.7, 1.8 Hz, ...
Embodiment 2
[0018] Example 2 Synthesis of 2-phenyl-1,3-bis(p-methylphenylthio)indoxazine
[0019] Add 2-phenylindolezine (0.26 mmol, 0.050 g) and p-cresol (0.54 mmol, 0.067 g), KI (10 mol%, 0.005 g), DCE (1 mL) into a 25 mL reaction flask. The reaction was stirred under an air atmosphere at 60 °C until the reaction was completed, the reaction time was 24 h, and the reaction was quenched with saturated sodium thiosulfate. Then the reaction mixture was diluted with 5ml ethyl acetate and 10ml water, extracted with 10ml ethyl acetate, the organic layer was washed with 10ml saturated saline, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with petroleum ether:ethyl acetate=300:1, to obtain 69 mg of white solid 2-phenyl-1,3-bis(p-tolylthio)indolezine, yield 61%.
Embodiment 3
[0020] Example 3 Synthesis of 2-phenyl-1,3-bis(p-methylphenylthio)indoxazine
[0021] Add 2-phenylindolezine (0.26 mmol, 0.050 g) and p-cresol (0.54 mmol, 0.067 g), KI (10 mol%, 0.005 g), CHCN (1 mL) into a 25 mL reaction vial. The reaction was stirred with oxygen at 60 °C until the end of the reaction, the reaction time was 7 h, and the reaction was quenched with saturated sodium thiosulfate. Then the reaction mixture was diluted with 5ml ethyl acetate and 10ml water, extracted with 10ml ethyl acetate, washed the organic layer with 10ml saturated saline, dried over anhydrous sodium sulfate, and distilled under reduced pressure. The crude product was purified by silica gel chromatography, eluting with petroleum ether:ethyl acetate=300:1, to obtain 72 mg of 2-phenyl-1,3-bis(p-tolylthio)indolezine as a white solid, with a yield of 63%.
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