Phenanthridine compound and synthesis method thereof

A synthesis method and compound technology, applied in organic chemistry and other fields, can solve the problems of low functional group tolerance, few reports, high reaction cost, etc., and achieve the effect of cheap reaction raw materials, easy operation, and lower reaction temperature

Active Publication Date: 2019-12-31
SHAANXI UNIV OF SCI & TECH
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Problems solved by technology

The method of traditional synthetic phenanthridine compounds is mainly Pictet-Hubert method [a) Pictet, Ame; Hubert, ABer.Dtsch.Chem.Ges.1896,29,1182.], this method reaction time is long, high temperature, and the Low functional group tolerance
Synthesis of phenanthridine by hydrocarbon functionalization is an efficient and highly functional group-tolerant method developed in recent years [b) Han, W.Y.; Zhou, X.J.; Yang, S.Y.; Xiang, G.Y.; Cui, B.D.; Chen, Y.Z.J.Org .Chem.2015,80,11580.c)Ge,J.;Wang,X.J.;Liu,T.Q.;Shi,Z.Y.;Xiao,Q.;Yin,D.L.RSC Adv.2016,6,19571.d)Gao,Y.Z. ; Cai, Z.H.; Li, S.D.; Li, G.Org.Let.2019,21,3663.], but this kind of method needs to add transition metal catalyst and various additives, the reaction cost is high and pollutes the environment
Therefore, the method of synthesizing phenanthridine compounds efficiently and conveniently without metal catalyst is of great significance [e) Hofstra, J.L.; Grassbaugh, B.R.; Tran, Q.M.; Armada, N.R.; De Lijser, H.J.P.J.Org.Chem. ) Chen, W.L.; Chen, C.Y.; Chen, Y.F.; Hsieh, J.C.Org. Let.2015, 17, 1613.], but such reports are few

Method used

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  • Phenanthridine compound and synthesis method thereof
  • Phenanthridine compound and synthesis method thereof
  • Phenanthridine compound and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Preparation of Ethylphenanthridine-6-carboxylate

[0065] 0.2 mmol of 1,1'-diphenyl-2-amine, 1.5 equivalents of ethyl 2-diazobenzoylacetate and 1.6 mL of CF 3 Add COOH to a 15mL pressure-resistant tube (equipped with a magnetic stirrer), stir at 120°C under oxygen, monitor the progress of the reaction with TLC, and extract three times with 15mL ethyl acetate and saturated 15*3mL sodium bicarbonate solution after the reaction is complete , the combined organic phases were concentrated and separated by silica gel column chromatography to obtain 38.2 mg of light yellow solid compound with a yield of 76%. The structural formula of the resulting product is as follows:

[0066]

[0067] like figure 1 and figure 2 Shown, product NMR characterization: 1 H NMR (400MHz, CDCl 3 ):δ8.64(d,J=8.3Hz,1H),8.59-8.51(m,2H),8.29(d,J=7.6Hz,1H),7.86(t,J=7.2Hz,1H),7.80 -7.67(m,3H),4.64(q,J=7.1Hz,2H),1.53(t,J=7.1Hz,3H). 13 C NMR (100MHz, CDCl 3 ): δ166.3, 151.1, 142.6, 133.3, 131.1,...

Embodiment 2

[0070] Preparation of Ethyl 8-methylphenanthridine-6-carboxylate

[0071] Mix 0.2 mmol of 4'-methyl-1,1'-diphenyl-2-amine, 1.5 equivalents of ethyl 2-diazobenzoylacetate and 1.6 mL of CF 3 Add COOH to a 15mL pressure-resistant tube (equipped with a magnetic stirrer), stir at 120°C under oxygen, monitor the progress of the reaction with TLC, and extract three times with 15mL ethyl acetate and saturated 15*3mL sodium bicarbonate solution after the reaction is complete , the combined organic phases were concentrated and separated by silica gel column chromatography to obtain 38.2 mg of a white solid compound with a yield of 72%. The structural formula of the resulting product is as follows:

[0072]

[0073] like image 3 and Figure 4 Shown, product NMR characterization: 1 H NMR (400MHz, CDCl 3 ): δ8.55(d, J=8.5Hz, 2H), 8.30(s, 1H), 8.29-8.24(m, 1H), 7.82-7.64(m, 3H), 4.64(q, J=7.1Hz, 2H), 2.60(s, 3H), 1.54(t, J=7.1Hz, 3H). 13 C NMR (100MHz, CDCl 3 ): δ166.4, 150.8, 14...

Embodiment 3

[0076] Preparation of Ethyl 8-methoxyphenanthridine-6-carboxylate

[0077] Mix 0.2 mmol of 4'-methoxy-1,1'-diphenyl-2-amine, 1.5 equivalents of ethyl 2-diazobenzoylacetate and 1.6 mL of CF 3 Add COOH to a 15mL pressure-resistant tube (equipped with a magnetic stirrer), stir at 120°C under oxygen, monitor the progress of the reaction with TLC, and extract three times with 15mL ethyl acetate and saturated 15*3mL sodium bicarbonate solution after the reaction is complete , the combined organic phases were concentrated and separated by silica gel column chromatography to obtain 37.7 mg of a white solid compound with a yield of 67%. The structural formula of the resulting product is as follows:

[0078]

[0079] like Figure 5 and Image 6 Shown, product NMR characterization: 1 H NMR (400MHz, CDCl 3 ):δ8.56(d,J=9.1Hz,1H),8.51-8.47(m,1H),8.29-8.24(m,1H),8.03(d,J=2.6Hz,1H),7.73-7.70( m,2H),7.50(dd,J=9.1,2.6Hz,1H),4.64(q,J=7.1Hz,2H),3.99(s,3H),1.55(t,J=7.1Hz,3H). 13 C NMR (10...

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Abstract

The invention discloses a phenanthridine compound and a synthesis method thereof. An aromatic amine compound and a diazocarbonyl compound are added into a solvent, reacting is carried out in an oxygenenvironment, and then separating and purifying are carried out to obtain the phenanthridine compound. The invention provides the method for synthesizing the phenanthridine compound by taking the aromatic amine and the diazocarbonyl compound as raw materials for the first time. The method is simple and efficient, does not need metal catalysts, and has wide applicability of substrates.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a phenanthridine compound and a synthesis method thereof. Background technique [0002] Phenanthridine compounds widely exist in natural products, drug molecules and functional materials, and are an important class of chemical skeletons. The method of traditional synthetic phenanthridine compounds is mainly Pictet-Hubert method [a) Pictet, Ame; Hubert, ABer.Dtsch.Chem.Ges.1896,29,1182.], this method reaction time is long, high temperature, and the Functional group tolerance is low. Synthesis of phenanthridine by hydrocarbon functionalization is an efficient and highly functional group-tolerant method developed in recent years [b) Han, W.Y.; Zhou, X.J.; Yang, S.Y.; Xiang, G.Y.; Cui, B.D.; Chen, Y.Z.J.Org .Chem.2015,80,11580.c)Ge,J.;Wang,X.J.;Liu,T.Q.;Shi,Z.Y.;Xiao,Q.;Yin,D.L.RSC Adv.2016,6,19571.d)Gao,Y.Z. ; Cai, Z.H.; Li, S.D.; Li, G.Org.Let.2019,21,3663.], but thi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/12C07D491/056C07D221/18C07D471/04C07D495/04C07D491/048
CPCC07D221/12C07D491/056C07D221/18C07D471/04C07D495/04C07D491/048
Inventor 南江马琼陈璞胡岩马养民
Owner SHAANXI UNIV OF SCI & TECH
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