Synthetic method of N-(2-phenylol)-beta-carboline and N-(5-chlorine-2-phenylol)-beta-carboline
A synthesis method and phenol-based technology are applied in the synthesis field of N--β-carboline and N--β-carboline, can solve problems such as unreported synthesis methods, and achieve simple and easy operation of synthesis process and simple raw materials. , The effect of the product is easy
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Embodiment 1
[0029] Example 1: Preparation of N-(2-phenolyl)-β-carboline
[0030] To a 25 mL sealed tube, add β-carboline nitrogen oxide (1.0 mmol, 184 mg), diphenyl periodonium salt (1.0 mmol), and after purging nitrogen three times, add 1,2-dichloroethane (3 mL). The system was stirred at room temperature for 15-30 minutes to make the system evenly mixed, and the sealed tube was moved into an oil bath to react at 120° C. for 2 days. After the reaction was completed, the system was cooled to room temperature. The system solution was concentrated and spin-dried to obtain a crude product. The crude product was separated by column chromatography (200-300 mesh silica gel) with dichloromethane: petroleum ether: methanol = 5: 3: 1 as the eluent to obtain a yellow solid product with a purity greater than 99% N-(2-phenolic )-β-carboline in 82% isolated yield.
[0031] Structural identification of N-(2-phenolyl)-β-carboline (Reticulatol):
[0032] NMR data:
[0033] 1 H NMR (400 MHz, METHAN...
Embodiment 2
[0037] Example 2: Preparation of N-(5-bromo-2-phenolyl)-β-carboline
[0038] To a 25 mL sealed tube, add β-carboline nitroxide (1.0 mmol, 184 mg), bis(p-bromophenyl) hypervalent iodide salt (1.0 mmol), and after purging nitrogen three times, add 1,2- Dichloroethane (3 mL). The system was stirred at room temperature for 15-30 minutes to make the system evenly mixed, and the sealed tube was moved into an oil bath to react at 120° C. for 2 days. After the reaction was completed, the system was cooled to room temperature. The system solution was concentrated and spin-dried to obtain a crude product. The crude product was separated by column chromatography (200-300 mesh silica gel) with dichloromethane: petroleum ether: methanol = 5: 3: 1 as the eluent to obtain a yellow solid product with a purity greater than 99% N-2-(5- bromophenol)carboline in 80% isolated yield.
[0039] NMR data:
[0040] 1 H NMR (301 MHz, METHANOL-D4) δ 9.10 (s, 1H), 8.48 (d, J = 6.5 Hz, 1H), 8.38 (d, ...
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