CN106632194A - Method for preparing benzopyrone compound through adopting pentacarbonyl iron as CO release source - Google Patents

Method for preparing benzopyrone compound through adopting pentacarbonyl iron as CO release source Download PDF

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CN106632194A
CN106632194A CN201610864108.4A CN201610864108A CN106632194A CN 106632194 A CN106632194 A CN 106632194A CN 201610864108 A CN201610864108 A CN 201610864108A CN 106632194 A CN106632194 A CN 106632194A
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benzofurantone
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iron pentacarbonyl
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CN106632194B (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 method for preparing a benzopyrone compound through adopting pentacarbonyl iron as a CO release source. The method comprises the step of subjecting a 2-iodophenol compound and terminal alkyne to a coupling reaction under mild conditions in a manner of taking palladium acetate as a catalyst, taking piperazine as a base and taking the pentacarbonyl iron as the CO release source, so as to produce the benzopyrone compound. According to the method, the operation is simple, the reaction conditions are mild, the consumption of the catalyst is low, the consumption of the CO release source is low, the toxicity is relatively low, the cost is relatively low, the substrate applicability is high, and the yield of target object is high, so that the method can be extensively applied to the preparation of a natural product, i.e., the benzopyrone compound.

Description

The method that Benzofurantone compound is prepared as CO source of releases using iron pentacarbonyl
Technical field
The invention belongs to the synthesis technical field of Benzofurantone compound, and in particular to it is a kind of using iron pentacarbonyl as Carbon monoxide (CO) source of release, 2- iodobenzenes phenolic compound as reaction substrate, under conditions of it need not add any part, With palladium as catalyst, piperazine as alkali under conditions of, synthesize Benzofurantone compound method.
Background technology
Benzofurantone compound is a kind of natural products being widely present in plant, with extensive biological living Property, such as：Antibacterial, antimycotic, antiviral, anti-inflammatory, microtubulin-resisting etc., and it is identified a kind of first-selected in pharmaceutical intermediate Structure, it is significant in organic synthesis.Therefore, Benzofurantone chemical combination is prepared using a kind of simple method Thing, receives much concern in organic field and pharmaceutical field.
Used as carbonyl supply source, diethylamine is alkali, palladium and part concerted catalysis 2- iodobenzene phenol generalizations to early application CO gases Preparing Benzofurantone compound, reaction condition is harsher, relatively costly, and the reaction time is longer for compound and Terminal Acetylenes, and And generate with accessory substance.
The content of the invention
The technical problem to be solved is to overcome what existing Benzofurantone compound preparation method was present Shortcoming, there is provided one kind changes CO supply sources, without the need for adding that part, reaction condition are gentle, the reaction time is short, product is single, The preparation method of the high Benzofurantone compound of safe and efficient, yield.
Solving the technical scheme that adopted of above-mentioned technical problem is：With acetonitrile as solvent, palladium as catalyst, piperazine be Alkali, 2- iodobenzenes phenolic compound and Terminal Acetylenes, iron pentacarbonyl are reacted 8～15 hours at 20～60 DEG C, obtain benzopyrone Class compound.
Above-mentioned 2- iodobenzene phenolic compounds areR in formula1、R2、R3、R4Each independent representative H, Cl, Any one in Br, preferred R1、R4Represent H, R2、R3Respective independent representative Cl or Br.
Above-mentioned Terminal Acetylenes isR ' represents phenyl, C in formula1～C5Alkyl-substituted phenyl, C1～C2Alkoxyl takes For phenyl, C6～C8Any one in alkyl, 2- thienyls, preferred R ' represents phenyl, p-methylphenyl, to ethylphenyl, right Any one in methoxyphenyl, hexyl, 2- thienyls.
In above-mentioned preparation method, preferred 2- iodobenzenes phenolic compound is 1 with the mol ratio of Terminal Acetylenes:1.3～2.0, pentacarbonyl The addition of iron is the 20%～60% of 2- iodobenzene phenolic compound moles, and the addition of palladium is 2- iodobenzene phenols chemical combination The 1%～10% of thing mole, the addition of piperazine is 2.0～4.0 times of 2- iodobenzene phenolic compound moles.
The present invention, using iron pentacarbonyl as CO source of releases, is under the conditions of catalyst, piperazine are alkali, to make 2- iodobenzenes in palladium Benzofurantone compound generated and coupling reaction with Terminal Acetylenes in phenolic compound there is.Relative to directly with CO gases as carbonyl confession To source, the present invention reduces the requirement harsh to consersion unit using iron pentacarbonyl as CO source of releases, and toxicity is smaller, it is easy to Control, overcomes that CO gases toxicity is more inconvenient than larger, storage, reaction needs that certain pressure is higher to equipment requirement to be lacked Point.In addition, the present invention need not add part, used catalyst is stable to air and water, and simple to operate, reaction condition is gentle, instead Short between seasonable, Atom economy is high, and target product post processing is simple and yield is high, the Benzofurantone compound for preparing With extensive biologically active and medical value.
Specific embodiment
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-ones of preparation structure formula
By 0.11g (0.5mmol) 2- iodophenols, 72 μ L (0.75mmol) phenylacetylenes, 0.0056g (0.025mmol) acetic acid Palladium, 0.1293g (1.5mmol) piperazines and 30 μ L (0.15mmol) iron pentacarbonyls, 3mL anhydrous acetonitriles add Shrek pipe, 50 Stirring reaction 12 hours at DEG C, stop reaction, and room temperature is down to naturally, and pillar layer separation obtains yellow solid 2- phenyl -4H- benzene And pyrans -4- ketone, its yield is 95%, and structural characterization data are：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- methoxyphenyls) -4H- benzopyran-4-ones
In embodiment 1, phenylacetylene used equimolar 4- Methoxy-phenylacetylene replacement, other steps and embodiment 1 It is identical, yellow solid 2- (4- methoxyphenyls) -4H- benzopyran-4-ones are obtained, its yield is 94%, structural characterization data For：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- tolyls) -4H- benzopyran-4-ones
In embodiment 1, phenylacetylene used equimolar 4- methyl phenylacetylene replacement, other steps and the phase of embodiment 1 Together, yellow solid 2- (4- tolyls) -4H- benzopyran-4-ones are obtained, its yield is 94%, and structural characterization data are：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- ethylphenyls) -4H- benzopyran-4-ones
In embodiment 1, phenylacetylene used equimolar 4- Liquid Crystal Compounds Intermediate p-Ethyl-phenylacetylene replacement, other steps and the phase of embodiment 1 Together, yellow solid 2- (4- ethylphenyls) -4H- benzopyran-4-ones are obtained, its yield is 80%, and structural characterization data are：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 group phenyl) -4H- benzopyran-4-ones
In embodiment 1, phenylacetylene used equimolar 4- amyl group phenylacetylene replacement, other steps and the phase of embodiment 1 Together, yellow solid 2- (4- amyl group phenyl) -4H- benzopyran-4-ones are obtained, its yield is 78%, and structural characterization data are：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- thienyls) -4H- benzopyran-4-ones
In embodiment 1, phenylacetylene used equimolar 2- thiophene acetylene replacement, other steps and the phase of embodiment 1 Together, yellow solid 2- (2- thienyls) -4H- benzopyran-4-ones are obtained, its yield is 94%, and structural characterization data are：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-ones of preparation structure formula
In embodiment 1, phenylacetylene used is replaced with equimolar 1- hexin, and other steps are same as Example 1, obtain Yellow solid 2- butyl -4H- benzopyran-4-ones, its yield is 80%, and structural characterization data are：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-ones of the following 6- of preparation structure formula
In embodiment 1, the 2- iodophenols used chloro- 2- iodophenols replacement of equimolar 4-, other steps and embodiment 1 It is identical, the chloro- 2- phenyl -4H- benzopyran-4-ones of yellow solid 6- are obtained, its yield is 94%, and structural characterization data are：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- thienyls -4H- benzopyran-4-ones of the following 6- of preparation structure formula
In embodiment 1,2- iodophenols used are replaced with the chloro- 2- iodophenols of equimolar 4-, phenylacetylene equimolar 2- Thiophene acetylene is replaced, and other steps are same as Example 1, obtain the chloro- 2- thienyls -4H- benzopyran-4-ones of 6-, its receipts Rate is 96%, and structural characterization data are：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-ones of the following 6- of preparation structure formula
In embodiment 1,2- iodophenols used are replaced with the chloro- 2- iodophenols of equimolar 4-, phenylacetylene equimolar 1- Hexin is replaced, and other steps are same as Example 1, obtain the chloro- 2- butyl -4H- benzopyran-4-ones of yellow solid 6-, its receipts Rate is 95%, and structural characterization data are：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-ones of the following 6- of preparation structure formula
In embodiment 1,2- iodophenols used are replaced with the bromo- 2- iodophenols of equimolar 4-, phenylacetylene equimolar 1- Hexin is replaced, and other steps are same as Example 1, obtain the bromo- 2- phenyl -4H- benzopyran-4-ones of yellow solid 6-, its receipts Rate is 95%, and structural characterization data are：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- thienyls -4H- benzopyran-4-ones of the following 6- of preparation structure formula
In embodiment 1,2- iodophenols used are replaced with the bromo- 2- iodophenols of equimolar 4-, phenylacetylene equimolar 2- Thiophene acetylene is replaced, and other steps are same as Example 1, obtain the bromo- 2- thienyls -4H- chromene -4- of yellow solid 6- Ketone, its yield is 93%, and structural characterization data are：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- methoxyphenyls) -4H- benzopyran-4-ones
In embodiment 1,2- iodophenols used are replaced with the chloro- 2- iodophenols of equimolar 5-, phenylacetylene equimolar 4- Methoxy-phenylacetylene is replaced, and other steps are same as Example 1, obtain the chloro- 2- of yellow solid 7- (4- methoxyphenyls) -4H- Benzopyran-4-one, its yield is 95%, and structural characterization data are：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- thienyls -4H- benzopyran-4-ones of the following 7- of preparation structure formula
In embodiment 1,2- iodophenols used are replaced with the chloro- 2- iodophenols of equimolar 5-, phenylacetylene equimolar 2- Thiophene acetylene is replaced, and other steps are same as Example 1, obtain the chloro- 2- thienyls -4H- chromene -4- of yellow solid 7- Ketone, its yield is 97%.

Claims (9)

1. a kind of method that employing iron pentacarbonyl prepares Benzofurantone compound as CO source of releases, it is characterised in that：With Acetonitrile is solvent, palladium is catalyst, piperazine is alkali, by 2- iodobenzenes phenolic compound and Terminal Acetylenes, iron pentacarbonyl 20～60 React 8～15 hours at DEG C, obtain Benzofurantone compound.
2. employing iron pentacarbonyl according to claim 1 prepares the side of Benzofurantone compound as CO source of releases Method, it is characterised in that：Described 2- iodobenzene phenolic compounds areR in formula1、R2、R3、R4Respective independent generation Any one in table H, Cl, Br.
3. employing iron pentacarbonyl according to claim 2 prepares the side of Benzofurantone compound as CO source of releases Method, it is characterised in that：Described R1、R4Represent H, R2、R3Respective independent representative Cl or Br.
4. employing iron pentacarbonyl according to claim 1 prepares the side of Benzofurantone compound as CO source of releases Method, it is characterised in that：Described Terminal Acetylenes isR ' represents phenyl, C in formula1～C5Alkyl-substituted phenyl, C1～C2Alkane Epoxide substituted-phenyl, C6～C8Any one in alkyl, 2- thienyls.
5. employing iron pentacarbonyl according to claim 4 prepares the side of Benzofurantone compound as CO source of releases Method, it is characterised in that：The R ' represents phenyl, p-methylphenyl, to ethylphenyl, p-methoxyphenyl, hexyl, 2- thienyls In any one.
6. the employing iron pentacarbonyl according to Claims 1 to 5 any one prepares Benzofurantone as CO source of releases The method of compound, it is characterised in that：The 2- iodobenzenes phenolic compound is 1 with the mol ratio of Terminal Acetylenes:1.3～2.0.
7. the employing iron pentacarbonyl according to Claims 1 to 5 any one prepares Benzofurantone as CO source of releases The method of compound, it is characterised in that：The addition of the iron pentacarbonyl be 2- iodobenzene phenolic compound moles 20%～ 60%.
8. the employing iron pentacarbonyl according to Claims 1 to 5 any one prepares Benzofurantone as CO source of releases The method of compound, it is characterised in that：The addition of the palladium be 2- iodobenzene phenolic compound moles 1%～ 10%.
9. the employing iron pentacarbonyl according to Claims 1 to 5 any one prepares Benzofurantone as CO source of releases The method of compound, it is characterised in that：The addition of the piperazine is 2.0～4.0 times of 2- iodobenzene phenolic compound moles.
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