Phosphorus oxide indole derivative containing thiophene bridge as well as preparation method and application of phosphorus oxide indole derivative
A derivative, phosphorus oxide technology, applied in chemical instruments and methods, medical preparations containing active ingredients, compounds of Group 5/15 elements of the periodic table, etc., can solve the problems of high biological toxicity and complex preparation methods, etc. Achieve the effect of enhancing electronic capabilities, wide application prospects, and good biocompatibility
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[0067] The present invention also provides a method for preparing a thiophene bridge-containing phosphordyl oxide derivative, comprising the following steps:
[0068] The preparation of phosphordole oxide derivatives with one of structures I~IV, its chemical formula is as follows:
[0069]
[0070] Mix the monobromide with the target substituent, the terminal alkyne with the target substituent, the catalyst, and the organic solvent, and heat to reflux under nitrogen to perform a coupling reaction. After the reaction is completed, separate and purify to obtain an internal alkyne intermediate; The internal alkyne intermediate, ethyl substituted phenyl phosphonate, catalyst and organic solvent are mixed, and heated to reflux under nitrogen gas to carry out ring-forming reaction. After the reaction is completed, the compound is separated and purified to obtain the phosphine oxide derivative;
[0071] Structure is the preparation of the phosphordyl oxide derivative of V or VI, a...
Embodiment 1
[0094] A preparation method of a thiophene bridge-containing phosphordole oxide derivative (compound α-Th-TPA-β-CN-PIO and compound β-Th-TPA-α-CN-PIO), comprising the steps of:
[0095]
[0096] (1) Weigh 2.03g of compound 1 (synthesis reported in existing literature: Dyes Pigm.2018,149,843-850), 0.76g of compound 2, 175mg of bis(triphenylphosphine)palladium dichloride in a double-necked round bottom flask , 95mg of cuprous iodide and 131mg of triphenylphosphine, add 80mL of triethylamine and 20mL of ultra-dry tetrahydrofuran, repeat the ventilation three times, and reflux at 70°C for 8h under the protection of nitrogen; after cooling to room temperature, wash with saturated salt Water extraction was performed three times; followed by silica gel column chromatography using petroleum ether / dichloromethane (1 / 1v / v) as the eluent to obtain 1.81 g of a yellow solid (intermediate product 3), with a yield of 80%;
[0097] (2) Weigh 1.81g of compound 3, 1.36g of compound 4, and 1....
Embodiment 2
[0101] A synthetic method containing thiophene bridge-containing phosphordole oxide derivatives (compound α-Th-TPA-β-Py-PIO and compound β-Th-TPA-α-Py-PIO), comprising the steps of:
[0102]
[0103] (1) Weigh 2.03g of compound 1 (synthesis reported in existing literature: Dyes Pigm.2018,149,843-850), 0.52g of compound 2, 175mg of bis(triphenylphosphine)palladium dichloride in a double-necked round bottom flask , 95mg of cuprous iodide and 131mg of triphenylphosphine, add 80mL of triethylamine and 20mL of ultra-dry tetrahydrofuran, repeat the pumping and ventilation three times, and reflux at 70°C for 8h under the protection of nitrogen; after cooling to room temperature, wash with saturated saline Extracted three times; followed by silica gel column chromatography using petroleum ether / dichloromethane (1 / 1v / v) as the eluent to obtain 1.61 g of a yellow solid (intermediate product 3), with a yield of 70%;
[0104] (2) Weigh 1.61g of compound 3, 1.50g of compound 4, and 1.71...
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