CN106632194B - The method that Benzofurantone compound is prepared as CO source of release using iron pentacarbonyl - Google Patents

The method that Benzofurantone compound is prepared as CO source of release using iron pentacarbonyl Download PDF

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CN106632194B
CN106632194B CN201610864108.4A CN201610864108A CN106632194B CN 106632194 B CN106632194 B CN 106632194B CN 201610864108 A CN201610864108 A CN 201610864108A CN 106632194 B CN106632194 B CN 106632194B
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compound
source
release
benzofurantone
iron pentacarbonyl
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CN106632194A (en
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高子伟
杨丹丹
徐珊
张伟强
郑绍华
孙华明
张国防
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Shaanxi Normal University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention discloses a kind of methods for preparing Benzofurantone compound as CO source of release using iron pentacarbonyl, this method using palladium acetate as catalyst, piperazine is alkali, iron pentacarbonyl is CO source of release, make 2- iodobenzene phenolic compound and Terminal Acetylenes that coupling reaction occur under mild conditions, generates Benzofurantone compound.Operation of the present invention is simple, and reaction condition is mild, and catalyst amount is few, and CO source of release dosage is low, and toxicity is smaller, and cost is relatively low, and substrate applicability is wide, and target substance yield is high, can be widely used for the preparation of natural products Benzofurantone compound.

Description

The method that Benzofurantone compound is prepared as CO source of release using iron pentacarbonyl
Technical field
The invention belongs to the synthesis technical fields of Benzofurantone compound, and in particular to it is a kind of using iron pentacarbonyl as Carbon monoxide (CO) source of release, 2- iodobenzene phenolic compound is as reaction substrate, under conditions of not needing to add any ligand, Under conditions of being alkali as catalyst, piperazine using palladium acetate, the method that synthesizes Benzofurantone compound.
Background technique
Benzofurantone compound is a kind of natural products being widely present in plant, has extensive biology living Property, such as: antibacterial, antimycotic, antiviral, anti-inflammatory, microtubulin-resisting, and a kind of first choice is identified in pharmaceutical intermediate Structure, be of great significance in organic synthesis.Therefore, Benzofurantone chemical combination is prepared using a kind of simple method Object is concerned in organic field and pharmaceutical field.
For early application CO gas as carbonyl supply source, diethylamine is alkali, palladium and ligand concerted catalysis 2- iodobenzene phenol generalization Object and Terminal Acetylenes are closed to prepare Benzofurantone compound, reaction condition is harsher, and higher cost, the reaction time is longer, and And it is generated with by-product.
Summary of the invention
Technical problem to be solved by the present invention lies in overcome existing for existing Benzofurantone compound preparation method Disadvantage provides a kind of change CO supply source, without add ligand, reaction condition are mild, the reaction time is short, reaction product is single, The preparation method of Benzofurantone compound safe and efficient, yield is high.
Solving technical solution used by above-mentioned technical problem is: using acetonitrile as solvent, palladium acetate be catalyst, piperazine is 2- iodobenzene phenolic compound is reacted 8~15 hours at 20~60 DEG C with Terminal Acetylenes, iron pentacarbonyl, obtains benzopyrone by alkali Class compound.
Above-mentioned 2- iodobenzene phenolic compound isR in formula1、R2、R3、R4It is independent represent H, Cl, Any one in Br, preferably R1、R4Represent H, R2、R3It is independent to represent Cl or Br.
Above-mentioned Terminal Acetylenes isR ' represents phenyl, C in formula1~C5Alkyl-substituted phenyl, C1~C2Alkoxy takes For phenyl, C6~C8Any one in alkyl, 2- thienyl, preferably R ' represent phenyl, p-methylphenyl, to ethylphenyl, right Methoxyphenyl, hexyl, any one in 2- thienyl.
In above-mentioned preparation method, preferably the molar ratio of 2- iodobenzene phenolic compound and Terminal Acetylenes is 1:1.3~2.0, pentacarbonyl The additional amount of iron is the 20%~60% of 2- iodobenzene phenolic compound mole, and the additional amount of palladium acetate is 2- iodobenzene phenols chemical combination The 1%~10% of object mole, the additional amount of piperazine are 2.0~4.0 times of 2- iodobenzene phenolic compound mole.
The present invention is using iron pentacarbonyl as CO source of release, under the conditions of palladium acetate is catalyst, piperazine is alkali, makes 2- iodobenzene Phenolic compound and Terminal Acetylenes undergo coupling reaction to produce Benzofurantone compound.Relative to directly using CO gas as carbonyl confession To source, the present invention reduces the requirement to consersion unit harshness using iron pentacarbonyl as CO source of release, and toxicity is smaller, is easy to Control, overcomes that CO gas toxicity is bigger, storage is inconvenient, reaction needs certain pressure is relatively high to equipment requirement to lack Point.In addition, the present invention stablizes air and water without adding ligand, used catalyst, easy to operate, reaction condition is mild, instead Short between seasonable, Atom economy is high, and target product post-processing is simple and yield is high, the Benzofurantone compound being prepared With extensive bioactivity and medical value.
Specific embodiment
Below with reference to embodiment, the present invention is described in more detail, but invention which is intended to be protected is not limited only to this A little embodiments.
Embodiment 1
The following 2- phenyl -4H- benzopyran-4-one of preparation structure formula
By 0.11g (0.5mmol) 2- iodophenol, 72 μ L (0.75mmol) phenylacetylenes, 0.0056g (0.025mmol) acetic acid Shrek pipe is added in palladium, 0.1293g (1.5mmol) piperazine and 30 μ L (0.15mmol) iron pentacarbonyls, 3mL anhydrous acetonitrile, 50 It is stirred to react at DEG C 12 hours, stops reaction, be down to room temperature naturally, pillar layer separation obtains yellow solid 2- phenyl -4H- benzene And pyrans -4- ketone, yield 95%, structural characterization data are as follows:1H NMR(400MHz,CDCl3) δ 8.24 (d, J=9.5Hz, 1H), 7.93 (d, J=8.0Hz, 2H), 7.74-7.67 (m, 1H), 7.56 (dd, J=18.1,7.0Hz, 4H), 7.43 (t, J= 7.5Hz,1H),6.84(s,1H)；13C NMR(101MHz,CDCl3)δ178.63,163.60,156.45,133.93,131.98, 131.76,129.20,126.47,125.89,125.39,124.15,118.24,107.78,100.13。
Embodiment 2
The following 2- of preparation structure formula (4- methoxyphenyl) -4H- benzopyran-4-one
In embodiment 1, phenylacetylene used is replaced with equimolar 4- Methoxy-phenylacetylene, other steps and embodiment 1 It is identical, obtain yellow solid 2- (4- methoxyphenyl) -4H- benzopyran-4-one, yield 94%, structural characterization data Are as follows:1H NMR(400MHz,CDCl3) δ 8.23 (d, J=8.0Hz, 1H), 7.89 (d, J=8.8Hz, 2H), 7.68 (t, J= 7.6Hz, 1H), 7.54 (s, 1H), 7.41 (t, J=7.5Hz, 1H), 7.03 (d, J=8.7Hz, 2H), 6.75 (s, 1H), 3.89 (s,3H)；13C NMR(101MHz,CDCl3)δ178.68,163.92,162.71,156.72,133.70,128.16,125.83, 125.23,124.21,124.11,118.10,114.63,106.36,100.13,55.65。
Embodiment 3
The following 2- of preparation structure formula (4- tolyl) -4H- benzopyran-4-one
In embodiment 1, phenylacetylene used is replaced with equimolar 4- methyl phenylacetylene, other steps and 1 phase of embodiment Together, yellow solid 2- (4- tolyl) -4H- benzopyran-4-one, yield 94%, structural characterization data are obtained are as follows:1H NMR(400MHz,CDCl3) δ 8.22 (d, J=7.6Hz, 1H), 7.82 (d, J=8.1Hz, 2H), 7.68 (t, J=8.0Hz, 1H), 7.55 (d, J=8.4Hz, 1H), 7.41 (t, J=7.5Hz, 1H), 7.31 (d, J=8.1Hz, 2H), 6.79 (s, 1H), 2.43(s,3H)；13C NMR(101MHz,CDCl3)δ178.61,163.75,156.37,142.38,133.78,129.89, 129.07,126.35,125.80,125.25,124.11,118.17,107.09,21.65。
Embodiment 4
The following 2- of preparation structure formula (4- ethylphenyl) -4H- benzopyran-4-one
In embodiment 1, phenylacetylene used is replaced with equimolar 4- Liquid Crystal Compounds Intermediate p-Ethyl-phenylacetylene, other steps and 1 phase of embodiment Together, yellow solid 2- (4- ethylphenyl) -4H- benzopyran-4-one, yield 80%, structural characterization data are obtained are as follows:1H NMR(400MHz,CDCl3) δ 8.23 (d, J=8.0Hz, 1H), 7.85 (d, J=8.1Hz, 2H), 7.69 (t, J=7.7Hz, 1H), 7.56 (d, J=8.4Hz, 1H), 7.41 (t, J=7.5Hz, 1H), 7.35 (d, J=8.0Hz, 2H), 6.81 (s, 1H), 2.73 (q, J=7.6Hz, 2H), 1.28 (t, J=7.6Hz, 4H)；13C NMR(101MHz,CDCl3)δ178.61,163.80, 156.41,148.62,133.78,129.33,128.72,126.50,125.83,125.26,124.15,118.19,107.17, 28.97,15.37。
Embodiment 5
The following 2- of preparation structure formula (4- amyl phenyl) -4H- benzopyran-4-one
In embodiment 1, phenylacetylene used is replaced with equimolar 4- amyl phenylacetylene, other steps and 1 phase of embodiment Together, yellow solid 2- (4- amyl phenyl) -4H- benzopyran-4-one, yield 78%, structural characterization data are obtained are as follows:1H NMR(400MHz,CDCl3) δ 8.22 (d, J=7.9Hz, 1H), 7.83 (d, J=8.1Hz, 2H), 7.68 (t, J=7.6Hz, 1H), 7.55 (d, J=8.4Hz, 1H), 7.40 (t, J=7.5Hz, 1H), 7.32 (d, J=8.1Hz, 2H), 6.80 (s, 1H), 2.69-2.65 (m, 2H), 1.65 (dt, J=14.4,7.2Hz, 2H), 1.34 (d, J=3.4Hz, 4H), 0.90 (t, J= 6.7Hz,3H)；13C NMR(101MHz,CDCl3)δ178.58,163.77,156.36,147.37,133.75,129.23, 126.38,125.78,125.23,124.10,118.16,107.10,35.96,31.53,30.95,22.61,14.11。
Embodiment 6
The following 2- of preparation structure formula (2- thienyl) -4H- benzopyran-4-one
In embodiment 1, phenylacetylene used is replaced with equimolar 2- thiophene acetylene, other steps and 1 phase of embodiment Together, yellow solid 2- (2- thienyl) -4H- benzopyran-4-one, yield 94%, structural characterization data are obtained are as follows:1H NMR(400MHz,CDCl3) δ 8.19 (d, J=7.7Hz, 1H), 7.70 (d, J=3.6Hz, 1H), 7.66 (d, J=7.2Hz, 1H), 7.56 (d, J=4.9Hz, 1H), 7.51 (d, J=8.4Hz, 1H), 7.39 (t, J=7.5Hz, 1H), 7.19-7.14 (m, 1H),6.68(s,1H)；13C NMR(101MHz,CDCl3)δ178.00,159.13,156.01,135.24,133.84, 130.37,128.60,128.55,125.77,125.36,124.08,118.03,106.27。
Embodiment 7
The following 2- butyl -4H- benzopyran-4-one of preparation structure formula
In embodiment 1, phenylacetylene used is replaced with equimolar 1- hexin, other steps are same as Example 1, obtain Yellow solid 2- butyl -4H- benzopyran-4-one, yield 80%, structural characterization data are as follows:1H NMR(400MHz, CDCl3) δ 8.18 (d, J=7.9Hz, 1H), 7.64 (t, J=7.7Hz, 1H), 7.42 (d, J=8.4Hz, 1H), 7.37 (t, J= 7.5Hz, 1H), 6.18 (s, 1H), 2.62 (t, J=7.5Hz, 2H), 1.74 (dd, J=14.8,7.4Hz, 2H), 1.45 (dt, J =14.8,7.3Hz, 2H), 0.97 (t, J=7.3Hz, 3H)；13C NMR(101MHz,CDCl3)δ178.58,169.97, 156.68,133.53,125.82,125.02,123.91,117.98,109.96,34.18,29.00,22.25,13.86。
Embodiment 8
The chloro- 2- phenyl -4H- benzopyran-4-one of the following 6- of preparation structure formula
In embodiment 1,2- iodophenol used is replaced with the chloro- 2- iodophenol of equimolar 4-, other steps and embodiment 1 It is identical, obtain the chloro- 2- phenyl -4H- benzopyran-4-one of yellow solid 6-, yield 94%, structural characterization data are as follows:1H NMR(400MHz,CDCl3) δ 8.20 (d, J=2.5Hz, 1H), 7.92 (dd, J=7.6,1.5Hz, 2H), 7.65 (dd, J= 8.9,2.5Hz,1H),7.57-7.52(m,4H),6.84(s,1H)；13C NMR(101MHz,CDCl3)δ177.35,163.89, 154.76,134.13,132.02,131.62,131.39,129.29,126.51,125.38,125.11,119.97,107.69。
Embodiment 9
The chloro- 2- thienyl -4H- benzopyran-4-one of the following 6- of preparation structure formula
In embodiment 1,2- iodophenol used is replaced with the chloro- 2- iodophenol of equimolar 4-, phenylacetylene equimolar 2- Thiophene acetylene replacement, other steps are same as Example 1, obtain the chloro- 2- thienyl -4H- benzopyran-4-one of 6-, receive Rate is 96%, structural characterization data are as follows:1H NMR(400MHz,CDCl3) δ 8.17 (d, J=2.3Hz, 1H), 7.73 (d, J= 3.4Hz, 1H), 7.62 (dd, J=13.8,4.1Hz, 2H), 7.49 (d, J=8.9Hz, 1H), 7.22-7.16 (m, 1H), 6.69 (s,1H)；13C NMR(101MHz,CDCl3)δ176.75,159.41,154.36,134.90,134.03,131.40,130.78, 128.89,128.75,125.35,125.12,119.78,106.21。
Embodiment 10
The chloro- 2- butyl -4H- benzopyran-4-one of the following 6- of preparation structure formula
In embodiment 1,2- iodophenol used is replaced with the chloro- 2- iodophenol of equimolar 4-, phenylacetylene equimolar 1- Hexin replacement, other steps are same as Example 1, obtain the chloro- 2- butyl -4H- benzopyran-4-one of yellow solid 6-, receive Rate is 95%, structural characterization data are as follows:1H NMR(400MHz,CDCl3) δ 8.15 (s, 1H), 7.58 (d, J=10.6Hz, 1H), 7.38 (d, J=8.9Hz, 1H), 6.18 (s, 1H), 2.62 (t, J=7.6Hz, 2H), 1.75-1.69 (m, 2H), 1.46-1.41 (m, 2H), 0.96 (t, J=7.3Hz, 3H)；13C NMR(101MHz,CDCl3)δ177.35,170.38,155.09,133.84, 131.10,125.41,124.99,119.82,110.02,34.24,29.07,22.35,13.93。
Embodiment 11
The bromo- 2- phenyl -4H- benzopyran-4-one of the following 6- of preparation structure formula
In embodiment 1,2- iodophenol used is replaced with the bromo- 2- iodophenol of equimolar 4-, phenylacetylene equimolar 1- Hexin replacement, other steps are same as Example 1, obtain the bromo- 2- phenyl -4H- benzopyran-4-one of yellow solid 6-, receive Rate is 95%, structural characterization data are as follows:1H NMR(400MHz,CDCl3) δ 8.37 (d, J=2.3Hz, 1H), 7.92 (d, J= 6.4Hz, 2H), 7.79 (dd, J=8.8,2.3Hz, 1H), 7.55 (d, J=7.2Hz, 3H), 7.48 (d, J=8.9Hz, 1H), 6.84(s,1H)；13C NMR(101MHz,CDCl3)δ177.18,163.87,155.20,136.89,132.03,131.61, 129.29,128.59,126.50,125.49,120.20,118.85,107.77,100.14。
Embodiment 12
The bromo- 2- thienyl -4H- benzopyran-4-one of the following 6- of preparation structure formula
In embodiment 1,2- iodophenol used is replaced with the bromo- 2- iodophenol of equimolar 4-, phenylacetylene equimolar 2- Thiophene acetylene replacement, other steps are same as Example 1, obtain the bromo- 2- thienyl -4H- chromene -4- of yellow solid 6- Ketone, yield 93%, structural characterization data are as follows:1H NMR(400MHz,CDCl3) δ 8.33 (d, J=2.4Hz, 1H), 7.76 (dd, J=8.9,2.4Hz, 1H), 7.72 (d, J=3.8Hz, 1H), 7.60 (d, J=5.0Hz, 1H), 7.43 (d, J=8.9Hz, 1H),7.21-7.18(m,1H),6.70(s,1H)；13C NMR(101MHz,CDCl3)δ176.59,159.41,154.82, 136.81,134.90,130.79,128.90,128.76,128.55,125.49,120.02,118.87,106.29。
Embodiment 13
The chloro- 2- of the following 7- of preparation structure formula (4- methoxyphenyl) -4H- benzopyran-4-one
In embodiment 1,2- iodophenol used is replaced with the chloro- 2- iodophenol of equimolar 5-, phenylacetylene equimolar 4- Methoxy-phenylacetylene replacement, other steps are same as Example 1, obtain the chloro- 2- of yellow solid 7- (4- methoxyphenyl) -4H- Benzopyran-4-one, yield 95%, structural characterization data are as follows:1H NMR(400MHz,CDCl3) δ 8.18 (d, J= 2.5Hz, 1H), 7.86 (d, J=8.9Hz, 2H), 7.64-7.60 (m, 1H), 7.50 (d, J=8.9Hz, 1H), 7.02 (d, J= 8.9Hz,2H),6.74(s,1H),3.89(s,3H)；13C NMR(101MHz,CDCl3)δ177.31,163.91,162.77, 154.61,133.89,131.18,128.21,125.26,123.67,119.81,106.11,55.66。
Embodiment 14
The chloro- 2- thienyl -4H- benzopyran-4-one of the following 7- of preparation structure formula
In embodiment 1,2- iodophenol used is replaced with the chloro- 2- iodophenol of equimolar 5-, phenylacetylene equimolar 2- Thiophene acetylene replacement, other steps are same as Example 1, obtain the chloro- 2- thienyl -4H- chromene -4- of yellow solid 7- Ketone, yield 97%.

Claims (7)

1. a kind of method for preparing Benzofurantone compound as CO source of release using iron pentacarbonyl, it is characterised in that: with Acetonitrile is solvent, palladium acetate is catalyst, piperazine is alkali, by 2- iodobenzene phenolic compound and Terminal Acetylenes, iron pentacarbonyl 20~60 It is reacted 8~15 hours at DEG C, obtains Benzofurantone compound；
Above-mentioned 2- iodobenzene phenolic compound isR in formula1、R2、R3、R4It is independent to represent in H, Cl, Br Any one；
Above-mentioned Terminal Acetylenes isR ' represents phenyl, C in formula1~C5Alkyl-substituted phenyl, C1~C2It is alkoxy substituted Base, C6~C8Any one in alkyl, 2- thienyl.
2. the side according to claim 1 for preparing Benzofurantone compound as CO source of release using iron pentacarbonyl Method, it is characterised in that: the R1、R4Represent H, R2、R3It is independent to represent Cl or Br.
3. the side according to claim 1 for preparing Benzofurantone compound as CO source of release using iron pentacarbonyl Method, it is characterised in that: the R ' represents phenyl, p-methylphenyl, to ethylphenyl, p-methoxyphenyl, hexyl, 2- thienyl In any one.
4. according to any one of claims 1 to 3 prepare Benzofurantone as CO source of release using iron pentacarbonyl The method of compound, it is characterised in that: the molar ratio of the 2- iodobenzene phenolic compound and Terminal Acetylenes is 1:1.3~2.0.
5. according to any one of claims 1 to 3 prepare Benzofurantone as CO source of release using iron pentacarbonyl The method of compound, it is characterised in that: the additional amount of the iron pentacarbonyl be 2- iodobenzene phenolic compound mole 20%~ 60%.
6. according to any one of claims 1 to 3 prepare Benzofurantone as CO source of release using iron pentacarbonyl The method of compound, it is characterised in that: the additional amount of the palladium acetate be 2- iodobenzene phenolic compound mole 1%~ 10%.
7. according to any one of claims 1 to 3 prepare Benzofurantone as CO source of release using iron pentacarbonyl The method of compound, it is characterised in that: the additional amount of the piperazine is 2.0~4.0 times of 2- iodobenzene phenolic compound mole.
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