Preparation method of acetylenic ketone compound
A compound, the technology of acetylene ketone, which is applied in the field of preparation of acetylene ketone compounds, achieves the effects of broadening the scope of application, easy storage, and reducing costs
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[0026] The invention provides a preparation method of acetylene compounds, comprising:
[0027] The compound of the formula (II), the compound of the formula (III) and N-formyl saccharin are reacted in a non-aqueous solvent under the action of a catalyst and a base to obtain the acetylenic compound of the formula (I):
[0028] Ar 1 -Br formula II;
[0029] In formula II and formula I, Ar 1 selected from aryl, heteroaryl and derivatives thereof;
[0030] In formula III and formula I, R 1 selected from alkyl, aryl, heteroaryl, acyl and derivatives thereof.
[0031] In the process of preparing acetylenic compounds in the present invention, aryl bromides are selected as reaction substrates.
[0032] In the present invention, in the formula II and formula I, Ar 1 Preferably selected from substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 heteroaryl, more preferably selected from phenyl, p-methylphenyl, p-methoxyphenyl, p-acetyl phenyl, naphthyl, ...
Embodiment 1
[0058] Embodiment 1 Synthetic acetylene ketone 4a
[0059] React according to the following equation:
[0060]
[0061] Under nitrogen protection, bromobenzene 1a (0.16g, 1mmol), phenylacetylene 2a (0.21g, 2mmol), N-formyl saccharin 3 (0.42g, 2mmol), and potassium carbonate (0.55g, 4mmol) were added to toluene in sequence , and then palladium acetate (22mg, 0.1mmol) was added, sealed and placed in a 100°C oil bath with stirring and heating. TLC detection substrate disappears, and reaction finishes, and through silica gel column chromatography (V 石油醚 :V 乙醚 =100:2) obtain white solid 0.18g, detect through NMR (detection result such as figure 1 with figure 2 shown), MS detection, confirmed that the structure of the acetylenone compound prepared by the method provided in Example 1 is shown in 4a, and its yield was 87% based on bromobenzene 1a, and the purity was >99%.
[0062] The spectrogram analysis data is as follows:
[0063] 1 H NMR (500MHz, CDCl 3 )δ8.26–8.20(m,2...
Embodiment 2
[0067] React according to the following equation:
[0068]
[0069] The acetylenone compound was prepared according to the method of Example 1, the difference from Example 1 was that the 1a compound was replaced by the 1b compound.
[0070] After NMR detection (detection results such as image 3 with Figure 4 shown), MS detection, confirmed that the structure of the acetylenone compound prepared by the method provided in Example 2 is shown in 4b, and its yield was 91% based on 1b, and the purity was >99%.
[0071] The spectrogram analysis data is as follows:
[0072] 1 H NMR (500MHz, CDCl 3 )δ8.12(d, J=8.1Hz, 2H), 7.68(d, J=7.1Hz, 2H), 7.48(t, J=7.4Hz, 1H), 7.42(t, J=7.4Hz, 2H) ,7.31(d,J=7.9Hz,2H),2.45(s,3H).;
[0073] 13 C NMR (126MHz, cdcl 3 )δ177.86, 145.38, 134.67, 133.14, 130.81, 129.82, 129.69, 129.46, 128.77, 120.32, 92.75, 87.06, 21.98;
[0074] HRMS(ESI)m / z calculated C 16 h 12 O[M+H] + :221.0765, found 221.0757.
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