2-Methyl-1,8-naphthyridine compounds and their preparation methods and applications
A compound and methylation technology, applied in organic chemistry, drug combination, antineoplastic drugs, etc., can solve the problems of low yield of main reaction, low utilization rate of atoms, complex side reactions, etc., and achieve high utilization rate of atoms , Novel structure, simple side reaction effect
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Embodiment 1
[0076] 2-Methyl-7-phenyl-1,8-naphthyridine has the following structure:
[0077]
[0078] The preparation method of 2-methyl-7-phenyl-1,8-naphthyridine is as follows:
[0079] In a reaction vessel, 2-phenyl-1,8-naphthyridine (5mmol, 1g), potassium tert-butoxide (10mmol, 1.1g), methanol (5mmol, 0.02g), dimethylsulfoxide (10mL) Mix evenly, react at 80°C for 24 hours, cool to room temperature after the reaction, filter, and remove unreacted substances by rotary evaporation under reduced pressure to obtain the crude product, which is purified by column chromatography to obtain 2-methyl-7-benzene Base-1,8-naphthyridine, namely compound 2a. Compound 2a is a white solid, melting point (m.p.): 108.9-109.7°C.
[0080] The reaction scheme is as follows:
[0081]
[0082] The hydrogen spectrogram and carbon spectrogram of gained compound 2a are respectively as follows Figure 1a with Figure 1b As shown, the structural characterization data are as follows:
[0083] 1 H NMR (4...
Embodiment 2
[0087] 2-(3-methoxyphenyl)-7-methyl-1,8-naphthyridine has the following structure:
[0088]
[0089] The preparation method of 2-(3-methoxyphenyl)-7-methyl 1,8-naphthyridine is as follows:
[0090] In a reaction vessel, 2-(3-methoxyphenyl)-1,8-naphthyridine (5mmol, 1.2g), potassium tert-butoxide (10mmol, 1.1g), ethanol (5mmol, 0.02g), Mix dimethyl sulfoxide (10mL) evenly, react at 160°C for 5 hours, cool to room temperature after the reaction, filter, and rotary evaporate under reduced pressure to remove unreacted substances to obtain the crude product, which is purified by column chromatography to obtain 2-(3-methoxyphenyl)-7-methyl-1,8-naphthyridine, namely compound 2b, compound 2b is a white solid, melting point (m.p.): 136.2-137.9°C.
[0091] The reaction scheme is as follows:
[0092]
[0093] The hydrogen spectrogram and the carbon spectrogram of compound 2b obtained are respectively as follows Figure 2a with Figure 2b As shown, the structural characterizatio...
Embodiment 3
[0098] 2-(7-Methyl-1,8-naphthyridin-2-yl)thiazole has the following structure:
[0099]
[0100] The preparation method of 2-(7-methyl-1,8-naphthyridin-2-yl)thiazole is as follows:
[0101]In a reaction vessel, 2-(1,8-naphthyridin-2-yl)thiazole (5mmol, 1.1g), potassium tert-butoxide (10mmol, 1.1g), phenylethyl alcohol (5mmol, 0.6g), dimethyl sulfoxide (10mL) was mixed evenly, and reacted at 100°C for 8 hours. After the reaction was completed, it was cooled to room temperature, filtered, and evaporated under reduced pressure to remove unreacted substances to obtain a crude product. The crude product was purified by column chromatography to obtain 2- (7-Methyl-1,8-naphthyridin-2-yl)thiazole, compound 2c. Compound 2c is a brown solid, melting point (m.p.): 123.4-125.1°C;
[0102] The reaction scheme is as follows:
[0103]
[0104] The hydrogen spectrogram and carbon spectrogram of compound 2c obtained are as follows respectively Figure 3a with Figure 3b As shown, th...
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