A kind of synthetic method of synthesizing benzo[1,3]oxazine-2-thione by isothiocyanate and 2-sulfonylalkylphenol
A technology of sulfonyl alkylphenol and isothiocyanate, which is applied in the field of synthesis of benzo[1,3]oxazine-2-thione, can solve the problem of weak catalyst and o-QMs, short life, Not suitable for problems such as acidic catalysts
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Embodiment 1
[0039]
[0040] Take 0.2 mmol of 2-(α-phenyl-p-toluenesulfonyl)phenol in a reaction flask, add 2 mL of solvent, 0.3 mmol of phenyl isothiocyanate, and finally add 0.5 mmol of alkaline reagent. The temperature of the system was controlled at 25°C, the stirring was continued, and the reaction was tracked by spotting samples on a thin-layer chromatographic plate until the reaction of the raw materials was complete.
[0041] After the reaction is completed, a silica gel column is used for separation and purification, and the purified product is rotary evaporated to obtain the target product.
[0042] Using the above reaction formula, set up 10 parallel test groups, using different alkaline reagents, solvents and reaction times. Alkaline reagents are cesium carbonate Cs 2 CO 3 , potassium carbonate K 2 CO 3, Triethylamine TEA, 1,8-diazabicyclo[5.4.0]undec-7-ene DBU, tetramethylguanidine TMG. The solvents were dichloromethane DCM, tetrahydrofuran THF, and dioxane Dioxane, re...
Embodiment 2
[0048] According to the operating steps and reagent consumption of Example 1, in the reaction system, 2-(α-phenyl-p-toluenesulfonyl)phenol is mixed with 4-cyanophenyl isothiocyanate and 4-nitrophenyl isothiocyanate respectively. For the reaction of cyanate and ethyl isothiocyanate, the basic reagent is 0.5 mmol of cesium carbonate, and 2 mL of DCM is used as a solvent, and the reaction is continuously stirred at 25 ° C, and the reaction is completed after 12 hours.
[0049]
[0050]
[0051] According to the analysis of the above test results, one of the reaction raw materials is isothiocyanate with different electrical substituents. During the reaction process, it undergoes [4+2] cycloaddition with o-QMs to obtain different addition products. The yield of benzo[1,3]oxazine-2-thione will be significantly lower.
Embodiment 3
[0054] Raw materials: 2-(α-phenyl-p-toluenesulfonyl)phenol, phenyl isothiocyanate
[0055] Product: Chemical formula: C 20 h 15 NOS
[0056] Molecular weight: 318.4126
[0057] Structural formula:
[0058] Yield: 92%
[0059] 1 H NMR (500MHz, CDCl 3 )δ7.39–7.31(m,8H),7.21–7.14(m,3H),7.04(d,J=7.1Hz,3H),5.69(s,1H). 13 C NMR (125MHz, CDCl 3 )δ=182.9, 147.9, 143.8, 140.2, 129.6, 129.5, 129.2, 128.9, 128.5, 127.6, 127.4, 126.2, 125.5, 121.8, 116.5, 67.1. HRMS (ESI) Calcd for C 20 h 15 NOS[M+H] + :318.4121,Found:318.4126.
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