CN110156776A - A kind of preparation method of C-3 sweet-smelling formacyl indolizine class compound - Google Patents

A kind of preparation method of C-3 sweet-smelling formacyl indolizine class compound Download PDF

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CN110156776A
CN110156776A CN201910364517.1A CN201910364517A CN110156776A CN 110156776 A CN110156776 A CN 110156776A CN 201910364517 A CN201910364517 A CN 201910364517A CN 110156776 A CN110156776 A CN 110156776A
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sweet
follows
class compound
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smelling formacyl
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杨誉竹
方友来
柳小兰
何李生
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Key Laboratory of Natural Product Chemistry of Guizhou Academy of Sciences
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Key Laboratory of Natural Product Chemistry of Guizhou Academy of Sciences
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Abstract

The invention discloses a kind of preparation methods of C-3 sweet-smelling formacyl indolizine class compound; it include: that metallic addition, iodine, pyridine derivatives, aryl methyl ketone, electron deficient olefins and alkali are added in organic solvent; 80~100 DEG C are heated to be reacted; after reaction, purification process obtains the C-3 sweet-smelling formacyl indolizine class compound.It is easily operated provided by the present invention for the preparation method of C-3 sweet-smelling formacyl indolizine class compound; purification process is easy; substrate designability is strong; practicability is stronger; synthetic method in compared with the existing technology avoids the use of part toxic reagent, reduces the limitation for realizing this compound synthesis route.

Description

A kind of preparation method of C-3 sweet-smelling formacyl indolizine class compound
Technical field
The invention belongs to organic synthesis fields, and in particular to a kind of preparation method of C-3 sweet-smelling formacyl indolizine class compound.
Background technique
Indolizine compound is widely present in natural products and has bioactive molecule as a kind of important nitrogen-containing heterocycle In structure (Nat.Prod.Rep.2002,19,742).Compound containing C-3 sweet-smelling formacyl indolizine structure have it is anticonvulsion and Anti-inflammatory (Arch.Pharm.Chem.Life Sci.2006,339,133), antibacterial and it is antimycotic (Molecules 2008,13, 1066) and b-FGF expression tumor cell line (HUVEC) is inhibited to be proliferated (Preparation of 1,2,3-substituted indolizines as selective b-FGF antagonists and angiogenesis inhibitors for treatment of cancer and cardiovascular diseases:Fr.,2859997A1[P].2005-03-25) Equal physiological activity.
The method of current one-step synthesis C-3 sweet-smelling formacyl indolizine class compound reported in the literature mainly passes through bromobenzene second Ketone, pyridine and electron deficient olefins are in potassium bichromate (RSCAdv., 2015,5,41255) or a water acetic acid copper and sodium acetate (RSCAdv., 2012,2,8637) reaction obtains in a heated condition.The synthetic method has certain limitation, such as needs to use The heavy metal mantoquita of the heavy metal chromic salts or 3 times of equivalents measured to toxic Adam, cannot using relatively simple acetophenone as Beginning raw material etc..
Summary of the invention
The present invention provides a kind of preparation methods of C-3 sweet-smelling formacyl indolizine class compound, and the preparation method step is simple, Raw material is easy to get, and convenient for operation, experiment safety is high.Specific experimental program is as follows:
A kind of preparation method of C-3 sweet-smelling formacyl indolizine class compound, the preparation step of the compound includes: first will be golden Belong to additive, iodine, pyridine derivatives, aryl methyl ketone, electron deficient olefins and alkali and is added to the reactor equipped with organic solvent In, it is heated to temperature and is reacted for 80~100 DEG C, after reaction 12-20 hours, purification process obtains C-3 sweet-smelling formacyl indolizine Class compound；
The wherein structure formula (II) of the electron deficient olefins are as follows:
The structure formula (III) of the pyridine derivatives are as follows:
The structure formula (IV) of the aryl methyl ketone are as follows:
The structure formula (I) of the C-3 sweet-smelling formacyl indolizine class compound of synthesis are as follows:
In the formula (I)~formula (IV): R1The group of representative are as follows: be hydrogen, carbomethoxy, ethoxycarbonyl, phenyl therein It anticipates one kind；R2The group of representative are as follows: carbomethoxy, ethoxycarbonyl, cyano, benzoyl it is therein any one；R3The group of representative Are as follows: hydrogen, methyl, methoxyl group, phenyl it is therein any one；R4The group of representative are as follows: phenyl, 4- iodophenyl, naphthalene, furans Base, thienyl it is therein any one；The metallic addition is monovalence copper；The organic solvent is N- crassitude Ketone or N,N-dimethylformamide.
The wherein additive amount of reactant, with molar amount, ratio are as follows: electron deficient olefins: pyridine derivatives: aryl methyl ketone: Monovalence copper: iodine: alkali=1:2~4:2~4:0.1~0.4:3~5:7~9.
The monovalence copper is stannous chloride or cuprous iodide；The alkali is sodium carbonate or potassium carbonate.
In the present invention, available purification process process includes: washing, and extraction dries, filters, silica gel mixed sample most passes through afterwards It crosses column chromatographic purifying and obtains corresponding C-3 sweet-smelling formacyl indolizine class compound.
The pyridine derivatives and aryl methyl ketone, the dosage relative to the electron deficient olefins are excessively, as excellent Choosing, with molar amount, electron deficient olefins: pyridine derivatives: aryl methyl ketone: metallic copper: iodine: alkali=1:2~4:2~4: 0.1~0.4:3~5:7~9.
Preferably, the time of the reaction is 12-20 hours.
In the present invention, the organic solvent that raw material sufficiently dissolves can be made reaction, preferably polar solvent, polarity Solvent can effectively promote the progress of reaction, and as a further preference, the organic solvent is N-Methyl pyrrolidone Or n,N-Dimethylformamide, various raw materials can be with higher conversion at product at this time.
The dosage of the organic solvent can preferably dissolve raw material, what the electron deficient olefins of 0.3mmol used The amount of organic solvent is about 0.5~2mL.
Preferably, the monovalence copper additives are stannous chloride or cuprous iodide.
Preferably, the alkali is sodium carbonate or potassium carbonate.
Preferably, the solvent is N-Methyl pyrrolidone or n,N-Dimethylformamide.
Further preferred, the C-3 sweet-smelling formacyl indolizine class compound of preparation of above-mentioned preparation method, concrete structure formula are Any one in compound shown in formula (I-1)~formula (I-13):
The utility model has the advantages that compared with the existing technology, the beneficial effects of the present invention are embodied in: reaction raw materials are easy to get, the system Preparation Method is easily operated, and post-processing is easy；Can design the compound for synthesizing required structure according to actual needs, practicability compared with By force.
Detailed description of the invention
Fig. 1: C-3 sweet-smelling formacyl indolizine class compound (I) reaction equation
Specific embodiment
Embodiment 1~13
Copper additives, iodine, alkali, aryl methyl ketone (IV), pyrrole is added in the seal pipe of 10ml according to the raw material proportioning of table 1 Pyridine analog derivative (III), electron deficient olefins (II) and organic solvent 1ml, are mixed evenly；Wherein in table 1, A is protochloride Copper；B is cuprous iodide；C is sodium carbonate；D is potassium carbonate；E is N-Methyl pyrrolidone；F is N,N-dimethylformamide.
According to table 2 reaction condition after the reaction was completed, reaction solution is transferred to fill 10% hypo solution point It is shaken in liquid funnel, water phase is extracted with ethyl acetate three times, merges organic phase, and anhydrous sodium sulfate is added and dries, filters, filtrate adds Enter silica gel mixed sample, vacuumize and be spin-dried for solvent, by silica gel column chromatography (eluant, eluent is ethyl acetate and petroleum ether mixtures) purifying Obtain corresponding C-3 sweet-smelling formacyl indolizine class compound (I).
In Tables 1 and 2, T is reaction temperature, and t is the reaction time, and Ph is phenyl, and Bz is benzoyl, and CN is cyano, 4Me For 4 methyl, 4OMe is 4 methoxyl groups, and 4Ph is 4 phenyl, and 4I-Ph is to iodophenyl, and 1Nap is 1 naphthalene, 2-Furyl For 2 furyls, Th is 2 thienyls, and the specific structure of (I-1)~(I-13) is shown in structure confirmation data part below.
Reaction equation is as shown in Figure 1.
The raw material proportioning of 1 embodiment 1~13 of table
The reaction condition and result of 2 embodiment 1~13 of table
In order to further confirm that the preparation method reasonability and made of compound structure accuracy, using nuclear-magnetism Resonate to the carry out nuclear magnetic resonance of the C-3 sweet-smelling formacyl indolizine class compound being prepared in embodiment 1-13 (1H NMR and13C NMR) detection obtains following result:
Embodiment 1
The C-3 sweet-smelling formacyl indolizine class compound (I-1) being prepared nuclear magnetic resonance (1H NMR and13C NMR) detection Data are as follows:
1H NMR(400MHz,CDCl3) δ 9.96 (d, J=7.1Hz, 1H), 8.38 (d, J=8.9Hz, 1H), 7.83-7.77 (m, 3H), 7.57 (t, J=7.3Hz, 1H), 7.50 (t, J=7.3Hz, 2H), 7.44 (t, J=7.9Hz, 1H), 7.08 (t, J= 6.9Hz,1H),3.89(s,3H)。
13C NMR(100MHz,CDCl3)δ185.6,164.5,139.9,139.9,131.5,129.2,129.1,129.0, 128.4,127.9,122.6,119.5,115.4,105.9,51.3。
Embodiment 2
The C-3 sweet-smelling formacyl indolizine class compound (I-2) being prepared nuclear magnetic resonance (1H NMR and13C NMR) detection Data are as follows:
1H NMR(400MHz,CDCl3) δ 9.97 (d, J=7.0Hz, 1H), 8.39 (d, J=10.1Hz, 1H), 7.84- 7.78 (m, 3H), 7.57 (t, J=7.3Hz, 1H), 7.51 (t, J=7.3Hz, 2H), 7.47-7.42 (m, 1H), 7.08 (t, J= 6.3Hz, 1H), 4.37 (q, J=7.1Hz, 2H), 1.39 (t, J=7.1Hz, 3H).
13C NMR(100MHz,CDCl3)δ185.6,164.1,139.9,131.5,129.3,129.1,129.0,128.5, 127.8,122.5,119.5,115.4,106.3,60.2,14.6。
Embodiment 3
The C-3 sweet-smelling formacyl indolizine class compound (I-3) being prepared nuclear magnetic resonance (1H NMR and13C NMR) detection Data are as follows:
1H NMR(500MHz,CDCl3) δ 9.94 (d, J=7.1Hz, 1H), 7.82 (d, J=8.8Hz, 1H), 7.78 (d, J =7.7Hz, 2H), 7.61 (d, J=9.0Hz, 2H), 7.50 (dt, J=14.9,7.7Hz, 3H), 7.15 (t, J=7.0Hz, 1H)。
13C NMR(125MHz,CDCl3)δ185.2,141.3,139.2,132.1,129.6,129.4,129.0,128.6, 128.0,123.0,117.6,116.0,115.2,84.9。
Embodiment 4
The C-3 sweet-smelling formacyl indolizine class compound (I-4) being prepared nuclear magnetic resonance (1H NMR and13C NMR) detection Data are as follows:
1H NMR(400MHz,CDCl3) δ 9.62 (dt, J=7.1,1.1Hz, 1H), 8.37 (dt, J=9.1,1.3Hz, 1H), 7.70-7.65 (m, 2H), 7.57-7.52 (m, 1H), 7.46 (q, J=1.4Hz, 1H), 7.45-7.42 (m, 2H), 7.09 (td, J=7.0,1.4Hz, 1H), 3.87 (s, 3H), 3.30 (s, 3H).
13C NMR(100MHz,CDCl3)δ186.8,165.3,163.4,139.6,138.3,131.9,131.7,128.7, 128.6,128.6,128.2,128.1,120.0,116.1,104.0,52.3,51.7。
Embodiment 5
The C-3 sweet-smelling formacyl indolizine class compound (I-5) being prepared nuclear magnetic resonance (1H NMR and13C NMR) detection Data are as follows:
1H NMR(400MHz,CDCl3) δ 9.61 (dt, J=7.1,1.1Hz, 1H), 8.39 (dt, J=9.0,1.2Hz, 1H), 7.73-7.65 (m, 2H), 7.57-7.50 (m, 1H), 7.43 (td, J=7.7,1.1Hz, 3H), 7.08 (td, J=7.0, 1.4Hz, 1H), 4.33 (q, J=7.1Hz, 2H), 3.63 (q, J=7.2Hz, 2H), 1.33 (t, J=7.1Hz, 3H), 1.05 (t, J=7.2Hz, 3H).
13C NMR(100MHz,CDCl3)δ186.8,165.1,163.1,139.6,138.5,131.9,131.7,128.8, 128.5,128.1,128.0,120.6,119.9,115.9,104.2,65.7,64.4,30.8,30.0。
Embodiment 6
The C-3 sweet-smelling formacyl indolizine class compound (I-6) being prepared nuclear magnetic resonance (1H NMR and13C NMR) detection Data are as follows:
1H NMR(500MHz,CDCl3) δ 9.68 (dt, J=7.1,1.1Hz, 1H), 8.19 (dt, J=9.0,1.2Hz, 1H),7.44–7.41(m,2H),7.41–7.38(m,1H),7.37–7.34(m,2H),7.19–7.15(m,1H),7.11(tt,J =7.1,1.3Hz, 1H), 7.07 (td, J=6.9,1.4Hz, 1H), 7.05-7.00 (m, 2H), 6.98-6.93 (m, 2H), 6.85–6.83(m,2H),6.75–6.66(m,3H)。
13C NMR(100MHz,CDCl3)δ186.7,164.3,140.2,137.5,133.8,130.8,130.6,129.7, 129.5,128.4,128.2,127.1,126.6,126.4,125.4,124.5,123.9,119.6,115.7,106.1,51.3。
Embodiment 7
The C-3 sweet-smelling formacyl indolizine class compound (I-7) being prepared nuclear magnetic resonance (1H NMR and13C NMR) detection Data are as follows:
1H NMR(500MHz,CDCl3) δ 9.84 (d, J=7.1Hz, 1H), 8.16 (s, 1H), 7.81-7.78 (m, 2H), 7.77-7.75 (m, 1H), 7.59-7.54 (m, 1H), 7.50 (tt, J=6.7,1.5Hz, 2H), 6.93 (dd, J=7.1, 1.9Hz,1H),3.88(s,3H),2.49(s,3H)。
13C NMR(125MHz,CDCl3)δ185.4,164.7,140.5,140.0,139.7,131.4,129.5,129.0, 128.7,128.4,122.3,118.3,117.9,104.8,51.3,21.7。
Embodiment 8
The C-3 sweet-smelling formacyl indolizine class compound (I-8) being prepared nuclear magnetic resonance (1H NMR and13C NMR) detection Data are as follows:
1H NMR(500MHz,CDCl3) δ 9.78 (d, J=7.6Hz, 1H), 7.78 (s, 1H), 7.77 (s, 1H), 7.69- 7.65 (m, 2H), 7.54 (t, J=7.4Hz, 1H), 7.48 (t, J=7.4Hz, 2H), 6.72 (dd, J=7.7,2.8Hz, 1H), 3.93(s,3H),3.85(s,3H)。
13C NMR(100MHz,CDCl3)δ184.9,164.7,159.8,142.7,140.0,131.3,130.6,129.6, 128.9,128.3,121.8,109.1,104.1,97.4,55.8,51.1。
Embodiment 9
The C-3 sweet-smelling formacyl indolizine class compound (I-9) being prepared nuclear magnetic resonance (1H NMR and13C NMR) detection Data are as follows:
1H NMR(500MHz,CDCl3) δ 10.00 (d, J=7.2Hz, 1H), 8.63 (s, 1H), 7.85-7.81 (m, 3H), 7.77 (d, J=7.4Hz, 2H), 7.59 (t, J=6.8Hz, 1H), 7.52 (q, J=8.2,7.8Hz, 4H), 7.48-7.42 (m, 1H), 7.39 (d, J=5.9Hz, 1H), 3.92 (s, 3H).
13C NMR(125MHz,CDCl3)δ185.6,164.6,140.6,140.4,140.0,138.1,131.6,129.6, 129.4,129.3,129.0,128.5,127.2,122.5,116.3,114.8,106.3,51.4。
Embodiment 10
The C-3 sweet-smelling formacyl indolizine class compound (I-10) being prepared nuclear magnetic resonance (1H NMR and13C NMR) detection Data are as follows:
1H NMR(400MHz,CDCl3) δ 9.92 (dt, J=7.1,1.1Hz, 1H), 8.39 (dt, J=8.9,1.3Hz, 1H), 7.89-7.81 (m, 2H), 7.76 (s, 1H), 7.55-7.51 (m, 2H), 7.50-7.44 (m, 1H), 7.10 (td, J= 7.0,1.4Hz,1H),3.89(s,3H)。
13C NMR(100MHz,CDCl3)δ184.5,164.4,140.1,139.2,137.7,130.5,129.3,128.9, 128.1,122.2,119.5,115.6,106.2,98.7,51.4。
Embodiment 11
The C-3 sweet-smelling formacyl indolizine class compound (I-11) being prepared nuclear magnetic resonance (1H NMR and13C NMR) detection Data are as follows:
1H NMR(400MHz,CDCl3) δ 10.18 (d, J=7.0Hz, 1H), 8.42 (d, J=8.9Hz, 1H), 8.11 (d, J =7.7Hz, 1H), 8.00 (d, J=8.3Hz, 1H), 7.92 (d, J=7.7Hz, 1H), 7.66 (dd, J=7.0,1.3Hz, 1H), 7.58 (s, 1H), 7.56-7.48 (m, 4H), 7.16 (td, J=6.9,1.4Hz, 1H), 3.83 (s, 3H).
13C NMR(100MHz,CDCl3)δ186.7,164.3,140.2,137.5,133.8,130.8,130.6,129.7, 129.5,128.4,128.2,127.1,126.6,126.4,125.4,124.5,123.9,119.6,115.7,106.1,51.3。
Embodiment 12
The C-3 sweet-smelling formacyl indolizine class compound (I-12) being prepared nuclear magnetic resonance (1H NMR and13C NMR) detection Data are as follows:
1H NMR(400MHz,CDCl3) δ 9.98 (dt, J=7.1,1.1Hz, 1H), 8.46 (s, 1H), 8.35 (dt, J= 8.9,1.2Hz, 1H), 7.67 (dd, J=1.7,0.9Hz, 1H), 7.41 (ddd, J=8.9,6.9,1.2Hz, 1H), 7.33 (dd, J=3.5,0.9Hz, 1H), 7.03 (td, J=7.0,1.4Hz, 1H), 6.58 (dd, J=3.6,1.7Hz, 1H), 3.92 (s, 3H)。
13C NMR(100MHz,CDCl3)δ170.9,164.5,153.2,145.8,139.7,129.3,127.8,127.6, 121.4,119.4,117.7,115.3,112.2,106.3,51.4。
Embodiment 13
The C-3 sweet-smelling formacyl indolizine class compound (I-13) being prepared nuclear magnetic resonance (1H NMR and13C NMR) detection Data are as follows:
1H NMR(400MHz,CDCl3) δ 9.81 (dt, J=7.1,1.1Hz, 1H), 8.36 (dt, J=9.0,1.3Hz, 1H), 8.11 (s, 1H), 7.80 (dd, J=3.8,1.2Hz, 1H), 7.65 (dd, J=5.0,1.2Hz, 1H), 7.41 (ddd, J= 8.9,6.9,1.2Hz, 1H), 7.18 (dd, J=5.0,3.7Hz, 1H), 7.04 (td, J=6.9,1.4Hz, 1H), 3.91 (s, 3H)。
13C NMR(100MHz,CDCl3)δ176.4,164.4,144.2,139.9,132.2,132.1,129.0,127.8, 127.7,127.2,122.2,119.5,115.3,106.0,51.4。

Claims (5)

1. a kind of preparation method of C-3 sweet-smelling formacyl indolizine class compound, which is characterized in that the preparation step packet of the compound It includes: metallic addition, iodine, pyridine derivatives, aryl methyl ketone, electron deficient olefins and alkali being added to equipped with organic molten first It in the reactor of agent, is heated to temperature and is reacted for 80~100 DEG C, after reaction 12-20 hours, purification process obtains C-3 virtue Formoxyl indolizine class compound；
The wherein structure formula (II) of the electron deficient olefins are as follows:
The structure formula (III) of the pyridine derivatives are as follows:
The structure formula (IV) of the aryl methyl ketone are as follows:
The structure formula (I) of the C-3 sweet-smelling formacyl indolizine class compound of synthesis are as follows:
In the formula (I)~formula (IV): R1The group of representative are as follows: therein any one for hydrogen, carbomethoxy, ethoxycarbonyl, phenyl Kind；R2The group of representative are as follows: carbomethoxy, ethoxycarbonyl, cyano, benzoyl it is therein any one；R3The group of representative are as follows: hydrogen, Methyl, methoxyl group, phenyl it is therein any one；R4The group of representative are as follows: phenyl, 4- iodophenyl, naphthalene, furyl, thiophene Base it is therein any one；The metallic addition is monovalence copper；The organic solvent be N-Methyl pyrrolidone or N, Dinethylformamide.
2. the preparation method of C-3 sweet-smelling formacyl indolizine class compound according to claim 1, which is characterized in that with mole The ratio of the additive amount of meter reactant are as follows: electron deficient olefins: pyridine derivatives: aryl methyl ketone: monovalence copper: iodine: alkali= 1:2~4:2~4:0.1~0.4:3~5:7~9.
3. the preparation method of C-3 sweet-smelling formacyl indolizine class compound according to claim 1, which is characterized in that described Monovalence copper is stannous chloride or cuprous iodide.
4. the preparation method of C-3 sweet-smelling formacyl indolizine class compound according to claim 1, which is characterized in that described Alkali is sodium carbonate or potassium carbonate.
5. a kind of, such as the C-3 sweet-smelling formacyl indolizine class compound of any one method preparation, feature exist according to claim 1~4 In concrete structure formula is any one in compound shown in formula (I-1)~formula (I-13):
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