CN114478375A - Preparation method of 3-alkenyl quinoline-2 (1H) ketone derivative - Google Patents
Preparation method of 3-alkenyl quinoline-2 (1H) ketone derivative Download PDFInfo
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- CN114478375A CN114478375A CN202210169835.4A CN202210169835A CN114478375A CN 114478375 A CN114478375 A CN 114478375A CN 202210169835 A CN202210169835 A CN 202210169835A CN 114478375 A CN114478375 A CN 114478375A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Abstract
The invention discloses a preparation method of a 3-alkenyl quinoline-2 (1H) ketone derivative, which comprises the following steps: reacting palladium acetate, tri (3-methoxyphenyl) phosphine, molybdenum carbonyl, cesium carbonate, tetrabutylammonium iodide, o-nitrobenzaldehyde and allyl aryl ether at 100 ℃ for 30 hours, and after the reaction is completed, carrying out post-treatment to obtain the 3-alkenyl quinoline-2 (1H) ketone derivative. The preparation method uses o-nitrobenzaldehyde as a nitrogen source and a formyl source, is simple to operate, has cheap and easily-obtained reaction starting raw materials, wide substrate functional group tolerance range and high reaction efficiency. Can synthesize a plurality of 3-alkenyl quinoline-2 (1H) ketone derivatives according to actual needs, is convenient to operate and widens the practicability of the method.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of a 3-alkenyl quinoline-2 (1H) ketone derivative.
Background
The nitrogen heterocyclic compound is widely existed in various natural products and bioactive compounds, particularly quinoline-2 (1H) -ketone and derivatives thereof as special construction units, show various pharmaceutical activities, and are often used as antibiotics, antitumor drugs, antiplatelet drugs, endothelin receptor antagonists and angiotensin II receptor antagonists (J.Med.chem.1997,40, 754-765). Some quinolin-2 (1H) -ones, such as nybomycin and deoxybomycin, have become effective antibacterial agents. In addition, the quinolin-2 (1H) one derivatives are useful as intermediates in organic synthesis and play a very important role (J.Am.chem.Soc.2002,124, 7982-7990). Therefore, the synthesis of quinoline-2 (1H) ketone derivatives attracts the attention of chemists, and the search for new methods for preparing such important nitrogen heterocyclic compounds has been a long-term goal of synthesis and medicinal chemistry.
Transition metal catalyzed carbonylation is one of the most economical and direct methods for the synthesis of carbonyl-containing compounds (Chem 2019,5, 526-. Since Heck and colleagues pioneered work in 1974, palladium-catalyzed carbonylation reactions have attracted extensive interest in both industrial and academic fields. Aryl and vinyl halides (or pseudohalides) have also gained intensive application and research in carbonylation reactions. In addition, allyl compounds, as a very challenging class of electrophiles, can be directly converted into β, γ -unsaturated carboxylic compounds. However, research on carbonylation reactions in which such compounds participate has been limited, and most carbonylation reactions use allyl chloride, acetate, carbonate, and phosphate as electrophiles. Allyl ethers are of much less interest than these allyl derivatives and remain a challenging target. Based on the characteristics of natural property, low toxicity, easy operation and the like of allyl ether, exploring a carbonylation reaction taking allyl ether as an electrophilic reagent is one of the hot spots which people pay attention to.
Based on this, we developed a palladium-catalyzed reductive aminocarbonylation of o-nitrobenzaldehyde and allyl aryl ether to 3-alkenylquinolin-2 (1H) one derivatives. The reaction takes o-nitrobenzaldehyde as a nitrogen source and a formyl source to synthesize various 3-alkenyl quinoline-2 (1H) ketone derivatives with good to excellent yield. Notably, this is the first example of the reaction of an allyl aryl ether involved in the aminocarbonylation of a 3-alkenylquinolin-2 (1H) one derivative.
Disclosure of Invention
The invention provides a preparation method of a 3-alkenyl quinoline-2 (1H) ketone derivative, which has the advantages of simple steps, cheap and easily-obtained reaction raw materials, compatibility with various functional groups and good reaction applicability, and provides a new direction for the synthesis of the 3-alkenyl quinoline-2 (1H) ketone derivative by taking o-nitrobenzaldehyde as a nitrogen source and a formyl source.
A preparation method of a 3-alkenyl quinoline-2 (1H) ketone derivative comprises the following steps: reacting a palladium catalyst, tri (3-methoxyphenyl) phosphine, molybdenum carbonyl, cesium carbonate, an additive, o-nitrobenzaldehyde and allyl aryl ether at 90-110 ℃ for 28-32 hours, and after the reaction is completed, carrying out post-treatment to obtain the 3-alkenyl quinoline-2 (1H) ketone derivative;
the structure of the o-nitrobenzaldehyde is shown as the formula (II):
the structure of the allyl aryl ether is shown as the formula (III):
the structure of the 3-alkenyl quinoline-2 (1H) ketone derivative is shown as the formula (I):
in formulae (I) to (III), R1，R2Independently is H or methyl; r3Is H, C1～C4Alkyl, substituted or unsubstituted aryl or heterocyclic; r4Is H, methoxy or halogen;
the substituent on the aryl is C1～C4Alkyl, methoxy, trifluoromethyl or halogen;
the molar ratio of the palladium catalyst, the tri (3-methoxyphenyl) phosphine, the cesium carbonate and the tetrabutylammonium iodide is 0.1:0.2:3: 3;
R4is meta.
The reaction formula is as follows:
in the present invention, the optional post-processing procedure includes: filtering, mixing the sample with silica gel, and finally purifying by column chromatography to obtain the corresponding 3-alkenyl quinoline-2 (1H) ketone derivative, wherein the purification by column chromatography is a technical means commonly used in the field.
Preferably, R4Is H, methoxy, F or Cl, in this case, the o-nitrobenzaldehyde is easily obtained, and the reaction yield is high.
Preferably, R1Is H or methyl; r2Is H or methyl; r3Is H, methyl, propyl, tert-butyl, 4-tert-butylphenyl, 4-methoxyphenyl, 4-trifluoromethylphenyl, 4-fluorophenyl, 4-chlorophenyl, 3-furyl, in which case the allyl aryl ether is readily available and the reaction yields are high.
The o-nitrobenzaldehyde and allyl aryl ether used to prepare the 3-alkenylquinolin-2 (1H) one derivatives are relatively inexpensive and widely available in nature, and preferably, the o-nitrobenzaldehyde: allyl aryl ether: a palladium catalyst is 1.2-1.5: 1: 0.05-0.1; as a further preference, the molar amount of o-nitrobenzaldehyde: allyl aryl ether: palladium catalyst 1.5:1: 0.1.
Preferably, the reaction time is 30 hours, and if the reaction time is too long, the reaction cost is increased, and on the contrary, it is difficult to ensure the completion of the reaction.
Preferably, the reaction is carried out in acetonitrile, the amount of acetonitrile used is sufficient to dissolve the starting material, and the amount of acetonitrile used is about 1 to 2mL for 0.2mmol of allyl aryl ether.
Preferably, the palladium catalyst is palladium acetate, which is relatively inexpensive among a large number of palladium catalysts, and the reaction efficiency is high when palladium acetate is used as the catalyst.
As a further preference, the 3-alkenyl quinolin-2 (1H) one derivative is one of the compounds represented by formula (I-1) to formula (I-5):
in the above preparation method, the o-nitrobenzaldehyde, allyl aryl ether, molybdenum carbonyl, palladium acetate, tris (3-methoxyphenyl) phosphine, tetrabutylammonium iodide and cesium carbonate are generally commercially available products, and can be conveniently obtained from the market.
Compared with the prior art, the invention has the beneficial effects that: the o-nitrobenzaldehyde is used as a nitrogen source and a formyl source, the preparation method is simple, the operation is easy, the post-treatment is simple and convenient, the reaction starting material is cheap and easy to obtain, the tolerance range of a substrate functional group is wide, and the reaction efficiency is high. Can synthesize various 3-alkenyl quinoline-2 (1H) ketone derivatives according to actual needs, and has strong practicability.
Detailed Description
The invention is further described with reference to specific examples.
Examples 1 to 15
Adding palladium acetate, tri (3-methoxyphenyl) phosphine, molybdenum carbonyl, cesium carbonate, tetrabutylammonium iodide, o-nitrobenzaldehyde (II) and allyl aryl ether (III) into a 15mL sealed tube according to the raw material ratio in Table 1, then adding acetonitrile (1mL), uniformly mixing and stirring, reacting according to the reaction conditions in Table 2, filtering after the reaction is finished, stirring a sample with silica gel, and purifying by column chromatography to obtain a corresponding 3-alkenyl quinoline-2 (1H) ketone derivative (I), wherein the reaction process is shown as the following formula:
TABLE 1 raw material addition amounts of examples 1 to 15
TABLE 2
In tables 1 and 2, T is the reaction temperature, T is the reaction time, Me is methyl, Pr is propyl, T-Bu is methyl, OMe is methoxy, CF is3Is trifluoromethyl.
Structure confirmation data of the compounds prepared in examples 1 to 5:
nuclear magnetic resonance of 3-alkenylquinolin-2 (1H) one derivative (I-1) prepared in example 1 (1)1H NMR and13c NMR) the data were:
1H NMR(400MHz,DMSO-d6)δ11.73(s,1H),7.78(s,1H),7.61–7.54(m,1H),7.39–7.33(m,1H),7.23–7.19(m,1H),7.11–7.01(m,1H),5.88–5.82(m,1H),5.14(s,1H),2.23–1.92(s,3H).
13C NMR(101MHz,DMSO-d6)δ161.0,140.1,138.1,136.0,132.0,130.1,128.0,121.8,119.2,117.5,114.5,22.4.
nuclear magnetic resonance of 3-alkenylquinolin-2 (1H) one derivative (I-2) prepared in example 2 ((I-2))1H NMR and13c NMR) the data were:
1H NMR(400MHz,DMSO-d6)δ11.79(s,1H),7.94(s,1H),7.64–7.57(m,1H),7.45–7.37(m,1H),7.28–7.22(m,1H),7.18–7.09(m,1H),6.75–6.61(m,1H),6.53–6.44(m,1H),2.21–2.10(m,2H),1.51–1.39(m,2H),0.95–0.83(m,3H).
13C NMR(101MHz,DMSO-d6)δ161.2,137.6,134.0,133.7,129.6,128.5,127.6,124.6,121.9,119.5,114.7,35.2,22.0,13.7.
nuclear magnetic resonance of 3-alkenylquinolin-2 (1H) one derivative (I-3) prepared in example 3 (II-3)1H NMR and13c NMR) the data were:
1H NMR(400MHz,DMSO-d6)δ11.89(s,1H),8.13(s,1H),7.66–7.63(m,1H),7.62(s,1H),7.43(m,3H),7.27(m,1H),7.22(m,1H),7.17–7.13(m,3H),2.27(s,3H).
13C NMR(101MHz,DMSO-d6)δ161.2,137.7,137.4,134.8,134.5,131.1,129.9,129.5,128.5,128.3,127.8,126.5,122.5,122.1,119.6,114.8,20.9.
nuclear magnetic resonance of 3-alkenylquinolin-2 (1H) one derivative (I-4) prepared in example 4 (II-1H)1H NMR and13c NMR) the data were:
1H NMR(400MHz,DMSO-d6)δ11.91(s,1H),8.04(s,1H),7.88(s,1H),7.71–7.60(m,3H),7.49–7.39(m,1H),7.31–7.23(m,1H),7.20–7.11(m,1H),7.02–6.93(m,1H),6.87–6.84(m,1H).
13C NMR(101MHz,DMSO-d6)δ161.2,144.5,142.2,137.6,134.8,129.9,128.2,127.7,124.9,123.4,122.0,121.9,119.6,114.8,107.4.
nuclear magnetic resonance of 3-alkenylquinolin-2 (1H) one derivative (I-5) prepared in example 5 ((I-5))1H NMR and13c NMR) the data were:
1H NMR(400 MHz,CDCl3)δ12.25(s,1H),7.39–7.32(m,1H),7.25(m,2H),5.88(m,1H),5.37(m,1H),2.24(s,3H).
13C NMR(101 MHz,CDCl3)δ163.1,158.2(d,J＝241.7 Hz),140.4,135.9(d,J＝3.2 Hz),134.5(d,J＝22.0 Hz),120.7(d,J＝9.3 Hz),118.7,118.6,118.5,117.1(d,J＝8.3 Hz),112.5(d,J＝22.7 Hz),22.6。
Claims (9)
1. a method for preparing a 3-alkenylquinolin-2 (1H) one derivative, comprising the steps of: reacting a palladium catalyst, a ligand, molybdenum carbonyl, alkali, an additive, o-nitrobenzaldehyde and allyl aryl ether at 90-110 ℃ for 28-32 hours, and after the reaction is completed, carrying out post-treatment to obtain the 3-alkenyl quinoline-2 (1H) ketone derivative;
the structure of the o-nitrobenzaldehyde is shown as the formula (II):
the structure of the allyl aryl ether is shown as the formula (III):
the structure of the 3-alkenyl quinoline-2 (1H) ketone derivative is shown as the formula (I):
in the formulae (I) to (III), R1，R2Independently is H or methyl; r3Is H, C1～C4Alkyl, substituted or unsubstituted aryl or heterocyclic; r4Is H, methoxy or halogen;
the substituents on the aryl areC1～C4Alkyl, methoxy, trifluoromethyl or halogen.
2. The method for preparing 3-alkenylquinolin-2 (1H) one derivative according to claim 1, wherein R is1Is H or methyl; r2Is H or methyl; r3Is H, methyl, propyl, tert-butyl, 4-tert-butylphenyl, 4-methoxyphenyl, 4-trifluoromethylphenyl, 4-fluorophenyl, 4-chlorophenyl, 3-furyl; r4Is H, methoxy, F or Cl.
3. The process for producing a 3-alkenylquinolin-2 (1H) one derivative according to claim 1, wherein the molar ratio of o-nitrobenzaldehyde: allyl aryl ether: molybdenum carbonyl: palladium catalyst: ligand: alkali: the additive is 1.2-1.5: 1: 1.2-1.5: 0.05-0.1: 0.1-0.2: 3-4.
4. The method for producing a 3-alkenylquinolin-2 (1H) one derivative according to claim 1, wherein the reaction is carried out using acetonitrile as a solvent.
5. The method of claim 1, wherein the palladium catalyst is palladium acetate.
6. The process for preparing a 3-alkenylquinolin-2 (1H) one derivative according to claim 1, wherein the ligand is tris (3-methoxyphenyl) phosphine.
7. The process for preparing a 3-alkenylquinolin-2 (1H) one derivative according to claim 1, wherein the base is cesium carbonate.
8. The method of claim 1, wherein the additive is tetrabutylammonium iodide.
9. The method for preparing a 3-alkenylquinolin-2 (1H) one derivative according to claim 1, wherein the 3-alkenylquinolin-2 (1H) one derivative is one of the compounds represented by formula (I-1) to formula (I-5):
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Cited By (2)
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| CN115286556A (en) * | 2022-09-02 | 2022-11-04 | 浙江理工大学 | Preparation method of ester compound containing indolone or isoquinoline-1, 3-diketone structure |
| CN115403520A (en) * | 2022-08-30 | 2022-11-29 | 浙江理工大学 | Preparation method of quinoline-2 (1H) -ketone derivative |
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| CN113045489A (en) * | 2021-03-09 | 2021-06-29 | 浙江理工大学 | Preparation method of 3-arylquinoline-2 (1H) ketone derivative |
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Cited By (4)
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| CN115403520A (en) * | 2022-08-30 | 2022-11-29 | 浙江理工大学 | Preparation method of quinoline-2 (1H) -ketone derivative |
| CN115403520B (en) * | 2022-08-30 | 2023-12-19 | 浙江理工大学 | Preparation method of quinoline-2 (1H) -ketone derivative |
| CN115286556A (en) * | 2022-09-02 | 2022-11-04 | 浙江理工大学 | Preparation method of ester compound containing indolone or isoquinoline-1, 3-diketone structure |
| CN115286556B (en) * | 2022-09-02 | 2023-10-03 | 浙江理工大学 | Preparation method of ester compound containing indolone or isoquinoline-1, 3-dione structure |
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