A kind of oxazaphosphorous heterocyclic compound and its preparation method and application
A technology of compound and phosphorus heterocycle, which is applied in the field of oxanitrophosphorus heterocycle compound and its preparation, triazine phosphorus heterocycle compound and its preparation field, can solve the problems of long design route, rare raw materials, restricting development, etc., and achieve long service life , good yield and little environmental pollution
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Embodiment 1
[0046] To synthesize 2,6,10-triphenyl-1,5,9-triazatriphenylene[1,12-cde:5,4-c'd'e':9,8-c”d” e”] Tris([1,2]nitrophosphorus) 2,6,10-trisulfide as an example, its structure is as follows:
[0047]
[0048] Under the protection of nitrogen, dissolve 273mg (1mmol) of 1,5,9-triaminotriphenylene in 15ml of anhydrous o-dichlorobenzene, add it to a 50ml two-necked bottle, add 0.4ml of triethylamine, and under the protection of inert gas , slowly add 0.12ml of phenylphosphorus dichloride solution, reflux at 180°C for 2 hours, add sulfur powder, cool down to room temperature, and stir overnight. The solvent was removed by rotary evaporation under reduced pressure, separated and purified by column chromatography to obtain a white solid with a yield of 29% and a melting point of 273-277°C.
[0049] The spectral data of the resulting product are as follows:
[0050] 1 H NMR (400MHz, DMSO) δ9.87(s, 3H), 8.08-7.92(m, 3H), 7.91-7.75(m, 6H), 7.55(d, J=24.7Hz, 12H). 13 C NMR(101MHz,DMSO)δ=1...
Embodiment 2
[0053] To synthesize 3,4,7,8,11,12-hexamethoxy-2,6,10-triphenyl-1,5,9-triazatriphenylene[1,12-cde:5,4 -c'd'e':9,8-c”d”e”] tris([1,2]nitrogen phosphorus) 2,6,10-trisulfide as an example, its structural formula is as follows:
[0054]
[0055] Under nitrogen protection, dissolve 453mg (1mmol) of 3,4,7,8,11,12-hexamethoxy-1,5,9-triaminotriphenylene in 15ml of anhydrous o-dichlorobenzene and add to 50ml In the two-neck flask, add 0.4ml triethylamine, under the protection of inert gas, slowly add 0.12ml phenyl phosphorus dichloride solution, reflux reaction at 180°C for 2 hours, add sulfur powder, cool down to room temperature, and stir overnight. The solvent was removed by rotary evaporation under reduced pressure, separated and purified by column chromatography to obtain a white solid with a yield of 35% and a melting point of 241-243°C.
[0056] The spectral data of the resulting product are as follows: 1 H NMR (400MHz, CDCl 3 )δ=8.34–7.95(m,0H),7.58(dd,J=12.9,9.3,0H),6.77...
Embodiment 3
[0059] To synthesize 2,6,10-triphenyl-1,5,9-triazatriphenylene[1,12-cde:5,4-c'd'e':9,8-c”d” e"] three ([1,2] nitrogen phosphorus) 2,6,10-trioxide as an example, its structural formula is as follows:
[0060]
[0061] 2,6,10-Triphenyl-1,5,9-Triazatriphenylene [1,12-cde:5,4-c'd'e':9,8-c”d”e "] Tris([1,2] nitrogen phosphorus) 2,6,10-trisulfide and m-chloroperoxybenzoic acid were added to a 25ml two-necked flask, cooled to -30°C, anhydrous dichloromethane was added dropwise, and the dropwise , stirred, continued to react for 1h, added 5ml of saturated sodium sulfite solution and 25ml of dichloromethane, separated, the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain a white solid with a yield of 85% and a melting point > 320°C.
[0062] The spectral data of the resulting product are as follows:
[0063] 1 H NMR (400MHz, DMSO) δ = 10.05 (d, J = 6.1, 3H), 8.00–7.84 (m, 3H), 7.79 (dt, J = 20.2, 6.8,...
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