Application of Diphenyltetrahydrobisindole Derivatives Catalyzed Asymmetric Mannich Reaction
A diphenyltetrahydrobisindole derivative, a technology for catalytic reaction, applied in catalytic reaction, organic compound/hydride/coordination complex catalyst, preparation of organic compound, etc., can solve catalyst preparation difficulties, stereoselectivity It has the advantages of easy industrial production, mild synthesis process conditions and high catalytic efficiency.
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Embodiment 1
[0030] The present embodiment is the preparation method of catalyst, and concrete synthetic method is as follows:
[0031]
[0032] Place 6,12-diphenyldibenzo[b,f][1,5]diazacyclooctatetraene (2g, 5.6mmol) and 10mL acetic acid in a single-necked flask, and then add zinc powder (5g, 76.9mmol), as CH 2 Cl 2 It was used as solvent (25mL), and reacted at 25°C. The reaction was monitored by TLC until the end of the reaction, and recrystallized with ethanol to obtain 1.6g of white solid, which was catalyst a, and the yield was 88%. Mp:206.2-207.6℃. 1 H NMR (300MHz, CDCl 3 )δ (ppm): 7.14-7.01 (m, 2H, NH), 6.99-7.95 (m, 12H, ArH), 6.79-6.77 (m, 4H, ArH), 4.58 (s, 2H, NH); 13 C NMR (75MHz, CDCl 3 )δ(ppm): 150.9, 141.3, 134.1, 129.1, 128.1, 127.2, 126.8, 124.6, 119.8, 110.1, 83.1; ESI-MS: m / z=361[M+1] + .
[0033] Catalysts b to f were obtained by the same synthesis method as above.
[0034] b: The yield was 83%. Mp:223.4-225.9℃. 1 H NMR (300MHz, CDCl 3 )δ (ppm): 7.24-7.10 ...
Embodiment 2
[0040] In this example, using p-aniline, benzaldehyde and cyclohexanone as substrates, the activity of the asymmetric Mannich reaction catalyzed by diphenyltetrahydroindole derivatives a to f was confirmed. The experimental method is: weigh aniline (1mmol), benzaldehyde (1mmol), cyclohexanone (1mmol) and catalyst (0.09mmol) respectively into test tubes, stir at 25°C, and react for 12 hours. Stop the reaction and recrystallize with ethanol to obtain the reaction product.
[0041] The results are shown in Table 1. It can be seen that when a is used as a catalyst, the reaction result is the best.
[0042]
[0043] Table 1 The reaction results of cyclohexanone, aniline and benzaldehyde under the catalysis of different catalysts
[0044]
Embodiment 3
[0046] In this example, using aniline, benzaldehyde and cyclohexanone as substrates, referring to the experimental method of Example 2, the main influencing factors of the asymmetric Mannich reaction catalyzed by catalyst a, such as catalyst dosage and reaction solvent, were systematically studied.
[0047] Result is as shown in table 2, and numbering is the best experimental result of 3, so the optimum experimental condition of the asymmetric Mannich reaction of catalyst a catalysis is: aniline / benzaldehyde / cyclohexanone=1:1:1 (molar ratio) , the amount of catalyst used is 3mmol% (the amount of the total substance of the reactants), the reaction temperature is 25° C., and the catalyst itself is used as a solvent.
[0048] Table 2 Effects of different experimental conditions on the asymmetric Mannich reaction catalyzed by catalyst a
[0049]
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