CN108148070B - Synthetic method of furanone isoquinolone compound - Google Patents
Synthetic method of furanone isoquinolone compound Download PDFInfo
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- CN108148070B CN108148070B CN201810226250.5A CN201810226250A CN108148070B CN 108148070 B CN108148070 B CN 108148070B CN 201810226250 A CN201810226250 A CN 201810226250A CN 108148070 B CN108148070 B CN 108148070B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
Abstract
The invention discloses a synthetic method of furanone isoquinolinone compounds, belonging to the technical field of organic synthesis. The furanone and isoquinolinone compound is synthesized by the one-pot tandem reaction of the N-alkoxy aryl formamide compound and the 4-hydroxy-2-alkynoate compound, has the advantages of simple and convenient operation, mild condition, wide substrate application range, good regioselectivity and the like, and is suitable for industrial production.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a synthetic method of furanone isoquinolinone compounds.
Background
Fused nitrogen/oxygen heterocyclic compounds are widely found in nature and tend to have good biological and pharmaceutical activity. For example, many of the clinically used drug molecules for cardiovascular and cerebrovascular diseases, AIDS and psychosis include a fused nitrogen/oxygen heterocycle structure. The furanone isoquinolone is an important member in condensed nitrogen/oxygen heterocyclic compounds, and the unique structure and function of the furanone isoquinolone enable the furanone isoquinolone to become effective herbicides, insecticides, bactericides and the like, so that the furanone isoquinolone has high research and application values. So far, there are not many methods for synthesizing furanone isoquinolinone compounds reported in literature, and these literature methods have the disadvantages of difficult obtainment of raw materials, complicated reaction steps, harsh reaction conditions, etc. Therefore, research and development of a novel method for synthesizing the furanone isoquinolone compound from simple and easily obtained raw materials through simple and convenient operation steps have important theoretical significance and important application value.
Disclosure of Invention
The technical problem solved by the invention is to provide a synthesis method of furanone isoquinolone compounds, the synthesis method synthesizes the furanone isoquinolone compounds through one-pot tandem reaction of N-alkoxy aryl formamide compounds and 4-hydroxy-2-alkynoate compounds, and the method has the advantages of simple and convenient operation, mild conditions, wide substrate application range, good regioselectivity and the like, and is suitable for industrial production.
The invention adopts the following technical scheme for solving the technical problems:
a synthetic method of furanone isoquinolone compounds is characterized in that the specific synthetic process is as follows: dissolving N-alkoxy aryl formamide compounds 1 and 4-hydroxy-2-alkynoate compounds 2 in a solvent, then adding a catalyst and an additive, and stirring and reacting at 80-120 ℃ in the atmosphere of air or nitrogen to obtain furanone and isoquinolinone compounds 3, wherein the reaction equation in the synthesis method is as follows:
wherein R is1Is hydrogen, fluorine, chlorine, bromine, C1-4Straight-chain or branched alkyl, methoxy, phenyl or substituted phenyl, the substituent on the phenyl ring of the substituted phenyl is fluorine, chlorine, bromine, methyl or methoxy, R2Is phenyl or C1-4Straight or branched alkyl, R3Is phenyl or C1-4Straight or branched alkyl, R4Is C1-4Straight or branched alkyl, R5Is C1-4Linear or branched alkyl, 1, 4-dioxane, methanol, isopropanol, acetonitrile or glycol dimethyl ether as solvent, and dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer as catalyst (RhCp Cl)2]2) The additive is cesium acetate, potassium fluoride, silver acetate, sodium acetate, potassium carbonate or sodium carbonate.
More preferably, the dosage ratio of the N-alkoxy aryl formamide compound 1, the 4-hydroxy-2-alkynoate compound 2, the catalyst and the additive is 1:1-2:0.025: 1-2.
A synthetic method of furanone isoquinolone compounds is characterized in that the specific synthetic process is as follows: dissolving N-alkoxy aryl formamide compounds 1 and 4-hydroxy-2-alkynoate compounds 4 in a solvent, then adding a catalyst and an additive, and stirring and reacting at 80-120 ℃ in the atmosphere of air or nitrogen to obtain furanone and isoquinolinone compounds 5, wherein the reaction equation in the synthesis method is as follows:
wherein R is1Is hydrogen, fluorine, chlorine, bromine, C1-4Straight-chain or branched alkyl, methoxy, phenyl or substituted phenyl, the substituent on the phenyl ring of the substituted phenyl is fluorine, chlorine, bromine, methyl or methoxy, R4Is C1-4Straight or branched alkyl, R5Is C1-4Straight chain or branched alkyl, n is 1, 2 or 3, the solvent is 1, 4-dioxane, methanol, isopropanol, acetonitrile or ethylene glycol dimethyl ether, and the catalyst is dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer ([ RhCp Cl)2]2) The additive is cesium acetate, potassium fluoride, silver acetate, sodium acetate, potassium carbonate or sodium carbonate.
More preferably, the dosage ratio of the N-alkoxy aryl formamide compound 1, the 4-hydroxy-2-alkynoate compound 4, the catalyst and the additive is 1:1-2:0.025: 1-2.
The invention has the following advantages: (1) the synthesis process is simple and efficient, the furanone and isoquinolinone compounds are directly obtained through one-pot series reaction of the N-alkoxy aryl formamide compounds and the 4-hydroxy-2-alkynoate compounds, namely, the hexabasic nitrogen heterocycle and the pentabasic oxygen heterocycle are simultaneously constructed through one-pot series reaction, and the synthesis efficiency is high; (2) the reaction condition is mild, and the operation is simple and convenient; (3) the application range of the substrate is wide; (4) the reaction area has good selectivity. Therefore, the invention provides a new method with high speed and high efficiency for the synthesis of the furanone isoquinolone compound.
Detailed Description
The present invention is described in further detail below with reference to examples, but it should not be construed that the scope of the above subject matter of the present invention is limited to the following examples, and that all the technologies realized based on the above subject matter of the present invention belong to the scope of the present invention.
Example 1
N-methoxybenzamide (1a,75.6mg,0.5mmol) and ethylene glycol dimethyl ether were added to a 15mL reaction tube(DME,3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol), dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer ([ RhCp Cl [)2]27.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol) were reacted under nitrogen at 100 ℃ for 12h with stirring, then cooled to room temperature with suction, the mother liquor was spin-dried over silica gel and isolated on silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (99.7mg, 87%). The characterization data for this compound are as follows:1H NMR(400MHz,DMSO-d6)δ:1.64(s,6H),7.59(t,J＝7.6Hz,1H),7.85(t,J＝8.0Hz,1H),8.23(d,J＝8.4Hz,1H),8.27(d,J＝7.6Hz,1H),12.73(br s,1H).13C NMR(100MHz,DMSO-d6)δ:24.6,80.8,97.5,122.1,124.6,127.5,127.8,131.7,133.8,163.0,163.2,167.1.HRMS calcd for C13H11NO3Na:252.0631[M+Na]+,found:252.0645。
example 2
To a 15mL reaction tube were added N-methoxybenzamide (1a,75.6mg,0.5mmol), 1, 4-dioxane (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp Cl [ ]2]2(7.7mg,0.0125mmol) and cesium acetate (192.0mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol 200/1) to give product 3a as a white solid (81.4mg, 71%).
Example 3
To a 15mL reaction tube were added N-methoxybenzamide (1a,75.6mg,0.5mmol), methanol (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp Cl [ ]2]2(7.7mg,0.0125mmol) and cesium acetate (192.0mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (65.3mg, 57%).
Example 4
To a 15mL reaction tube were added N-methoxybenzamide (1a,75.6mg,0.5mmol), isopropanol (3mL), 4-hydroxy-4-methyl-ethyl 2-pentynoate (2a,156.2mg,1.0mmol), [ RhCp Cl [ ]2]2(7.7mg,0.0125mmol) and cesium acetate (192.0mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (87.1mg, 76%).
Example 5
To a 15mL reaction tube were added N-methoxybenzamide (1a,75.6mg,0.5mmol), acetonitrile (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp Cl [ ]2]2(7.7mg,0.0125mmol) and cesium acetate (192.0mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol 200/1) to give product 3a as a white solid (66.5mg, 58%).
Example 6
To a 15mL reaction tube were added N-methoxybenzamide (1a,75.6mg,0.5mmol), ethylene glycol dimethyl ether (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp Cl [ ]2]2(7.7mg,0.0125mmol) and cesium acetate (192.0mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol 200/1) to give product 3a as a white solid (90.5mg, 79%).
Example 7
To a 15mL reaction tube were added N-methoxybenzamide (1a,75.6mg,0.5mmol), ethylene glycol dimethyl ether (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp Cl [ ]2]2(7.7mg,0.0125mmol) and silver acetate (166.9mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (90.5mg, 79%).
Example 8
Adding N-methoxybenzamide (1a,75.6mg,0.5mmol) into a 15mL reaction tube,Ethylene glycol dimethyl ether (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol), [ RhCp. Cl [ ]2]2(7.7mg,0.0125mmol) and sodium acetate (82.0mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol-200/1) to give product 3a as a white solid (83.7mg, 73%).
Example 9
To a 15mL reaction tube were added N-methoxybenzamide (1a,75.6mg,0.5mmol), ethylene glycol dimethyl ether (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp Cl [ ]2]2(7.7mg,0.0125mmol) and potassium acetate (98.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (89.4mg, 78%).
Example 10
To a 15mL reaction tube were added N-methoxybenzamide (1a,75.6mg,0.5mmol), ethylene glycol dimethyl ether (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp Cl [ ]2]2(7.7mg,0.0125mmol) and potassium carbonate (138.2mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating on silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (91.7mg, 80%).
Example 11
To a 15mL reaction tube were added N-methoxybenzamide (1a,75.6mg,0.5mmol), ethylene glycol dimethyl ether (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp Cl [ ]2]2(7.7mg,0.0125mmol) and sodium carbonate (106.0mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating on silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (87.1mg, 76%).
Example 12
Reaction at 15mLN-methoxybenzamide (1a,75.6mg,0.5mmol), ethylene glycol dimethyl ether (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp. Cl ] were added to the tube2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 80 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (91.7mg, 80%).
Example 13
To a 15mL reaction tube were added N-methoxybenzamide (1a,75.6mg,0.5mmol), ethylene glycol dimethyl ether (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), the mixture was stirred at 120 ℃ under nitrogen for 12h, then cooled to room temperature, filtered with suction, the mother liquor was spin-dried over silica gel and isolated on silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (97.4mg, 85%).
Example 14
To a 15mL reaction tube were added N-methoxybenzamide (1a,75.6mg,0.5mmol), ethylene glycol dimethyl ether (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (29.1mg,0.5mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (64.2mg, 56%).
Example 15
To a 15mL reaction tube were added N-methoxybenzamide (1a,75.6mg,0.5mmol), ethylene glycol dimethyl ether (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under an air atmosphere for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating with silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (79.1mg, 69%).
Example 16
To a 15mL reaction tube were added N-methoxybenzamide (1a,75.6mg,0.5mmol), ethylene glycol dimethyl ether (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,78.1mg,0.5mmol) and [ RhCp. multidot. Cl2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating on silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (52.7mg, 46%).
Example 17
To a 15mL reaction tube were added 1b (82.6mg,0.5mmol), DME (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp. multidot. Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating on silica gel column (dichloromethane/methanol ═ 200/1) to give product 3b as a white solid (98.5mg, 81%). The characterization data for this compound are as follows:1H NMR(400MHz,DMSO-d6)δ:1.64(s,6H),2.49(s,3H),7.41-7.43(m,1H),8.08(s,1H),8.13(d,J＝8.0Hz,1H),12.69(s,1H).13C NMR(100MHz,DMSO-d6)δ:21.5,24.6,80.7,97.2,121.8,122.3,127.8,128.8,131.7,144.3,162.8,163.4,167.2.HRMS calcd for C14H13NO3Na:266.0788[M+Na]+,found:266.0789。
example 18
To a 15mL reaction tube were added 1c (103.6mg,0.5mmol), DME (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp. multidot. Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), and the mixture was placed under a nitrogen atmosphereThe reaction was stirred at 100 ℃ for 12h, then cooled to room temperature, filtered with suction, the mother liquor was spin-dried over silica gel and isolated on a silica gel column (dichloromethane/methanol-200/1) to give product 3c (102.7mg, 72%) as a pale yellow solid. The characterization data for this compound are as follows:1H NMR(400MHz,DMSO-d6)δ:1.32(s,9H),1.62(s,6H),7.63(dd,J1＝8.4Hz,J2＝1.6Hz,1H),8.14(d,J＝8.4Hz,1H),8.28(d,J＝1.6Hz,1H),12.66(br s,1H).13C NMR(100MHz,DMSO-d6)δ:24.6,30.7,35.0,80.7,97.6,117.9,122.3,125.3,127.6,131.7,156.8,162.7,163.3,167.3.HRMS calcd for C17H19NO3Na:308.1257[M+Na],found:308.1262。
example 19
To a 15mL reaction tube were added 1d (90.6mg,0.5mmol), DME (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp. multidot. Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor on silica gel, and separating on silica gel column (dichloromethane/methanol ═ 200/1) to give product 3d as a white solid (101.1mg, 78%). The characterization data for this compound are as follows:1H NMR(600MHz,DMSO-d6)δ:1.64(s,6H),3.90(s,3H),7.15(d,J＝8.4Hz,1H),7.67(s,1H),8.14(d,J＝8.4Hz,1H),12.60(s,1H).13C NMR(100MHz,DMSO-d6)δ:24.6,55.6,80.7,97.1,103.8,116.1,117.9,129.9,133.8,162.5,163.4,163.9,167.2.HRMS calcd for C14H13NO4Na:282.0737[M+Na]+,found:282.0738。
example 20
A15 mL reaction tube was charged with 1e (84.6mg,0.5mmol), DME (3mL), 4-hydroxy-4-methyl-2-pentanAcetylenic acid ethyl ester (2a,156.2mg,1.0mmol), [ RhCp Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give product 3e as a white solid (74.2mg, 60%). The characterization data for this compound are as follows:1H NMR(600MHz,DMSO-d6)δ:1.65(s,6H),7.46(t,J＝9.0Hz,1H),7.89(d,J＝9.0Hz,1H),8.30-8.32(m,1H),12.85(s,1H).13C NMR(100MHz,DMSO-d6)δ:24.5,81.1,97.1(d,4JC-F＝3.1Hz),107.4(d,2JC-F＝23.0Hz),115.8(d,2JC-F＝23.5Hz),121.5,131.5(d,3JC-F＝10.9Hz),134.0(d,3JC-F＝11.2Hz),162.3,164.5,165.2(d,1JC-F＝251.1Hz),166.9.19F NMR(565MHz,DMSO-d6)δ:-103.91.HRMS calcd for C13H10FNO3Na:270.0537[M+Na]+,found:270.0537。
example 21
To a 15mL reaction tube were added 1f (113.6mg,0.5mmol), DME (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp. multidot. Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating on silica gel column (dichloromethane/methanol ═ 200/1) to give product 3f as a white solid (120.6mg, 79%). The characterization data for this compound are as follows:1H NMR(600MHz,DMSO-d6)δ:1.67(s,6H),7.49(t,J＝7.8Hz,1H),7.56(t,J＝7.2Hz,2H),7.76(d,J＝7.2Hz,2H),7.90(d,J＝8.4Hz,1H),8.31(d,J＝8.4Hz,1H),8.50(s,1H),12.77(s,1H).13C NMR(100MHz,DMSO-d6)δ:24.6,80.9,97.5,119.6,123.5,126.1,127.1,128.6,128.7,129.2,132.2,138.9,145.2,162.8,163.7,167.2.HRMS calcd for C19H16NO3:306.1125[M+H]+,found:306.1124。
example 22
To a 15mL reaction tube were added 1g (82.6mg,0.5mmol), DME (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp. multidot. Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), the mixture was stirred at 100 ℃ under nitrogen for 12h, then cooled to room temperature, filtered with suction, the mother liquor was spin-dried over silica gel and isolated on silica gel column (dichloromethane/methanol-200/1) to give 3g (103.4mg, 85%) of the product as a white solid. The characterization data for this compound are as follows:1H NMR(400MHz,DMSO-d6)δ:1.63(s,6H),2.44(s,3H),7.64-7.67(m,1H),8.01(s,1H),8.13(d,J＝8.0Hz,1H),12.63(br s,1H).13C NMR(100MHz,DMSO-d6)δ:21.0,24.6,80.7,97.5,122.0,124.5,127.4,129.2,134.9,137.1,162.3,162.8,167.2.HRMS calcd for C14H13NO3Na:266.0788[M+Na]+,found:266.0784。
example 23
To a 15mL reaction tube were added 1h (90.6mg,0.5mmol), DME (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp. Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating on silica gel column (dichloromethane/methanol ═ 200/1) to give the products as white solids, 3h (45.4mg, 35%) and 3h' (35.0mg, 27%). Characterization data for compound 3h are as follows:1H NMR(400MHz,DMSO-d6)δ:1.64(s,6H),3.89(s,3H),7.49(dd,J1＝8.4Hz,J2＝2.4Hz,1H),7.67(d,J＝2.4Hz,1H),8.20(d,J＝8.4Hz,1H),12.75(s,1H).13C NMR(100MHz,DMSO-d6)δ:24.7,55.4,80.8,97.6,109.0,122.9,123.8,125.2,126.1,158.5,160.9,162.6,167.3.HRMS calcd for C14H13NO4Na:282.0737[M+Na]+282.0737, found. Characterization data for compound 3h' are as follows:1H NMR(400MHz,CDCl3)δ:1.75(s,6H),3.97(s,3H),7.23(d,J＝7.6Hz,1H),7.49(t,J＝7.6Hz,1H),8.02(d,J＝7.6Hz,1H),13.43(s,1H).13C NMR(100MHz,CDCl3)δ:25.6,56.4,79.0,100.7,116.0,120.1 123.8,126.1,128.7,156.5,162.1,165.5,165.8.HRMS calcd for C14H13NO4Na:282.0737[M+Na]+,found:282.0747。
example 24
To a 15mL reaction tube were added 1i (92.8mg,0.5mmol), DME (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp. multidot. Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give the products 3i (25.0mg, 19%) and 3i' (47.5mg, 36%) as white solids. Characterization data for compound 3i are as follows:1H NMR(600MHz,DMSO-d6)δ:1.66(s,6H),7.90(d,J＝8.4Hz,1H),8.15(s,1H),8.26(d,J＝8.4Hz,1H),12.92(s,1H).13C NMR(100MHz,DMSO-d6)δ:24.5,81.1,97.3,124.2,126.1,126.9,130.4,132.0,133.9,161.9,163.4,166.9.HRMS calcd for C13H10ClNO3Na:286.0241[M+Na]+286.0243, found. Characterization data for compound 3i' are as follows:1H NMR(400MHz,DMSO-d6)δ:1.64(s,6H),7.58(t,J＝8.0Hz,1H),7.90(d,J＝8.0Hz,1H),8.28(d,J＝7.6Hz,1H),12.94(br s,1H).13C NMR(100MHz,DMSO-d6)δ:24.8,78.8,97.0,127.2,127.7,128.2,128.7,130.6,136.3,162.1,164.3,165.3.HRMS calcd for C13H10ClNO3Na:286.0241[M+Na]+,found:286.0245。
example 25
To a 15mL reaction tube were added 1j (115.0mg,0.5mmol), DME (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp. multidot. Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating on silica gel column (dichloromethane/methanol ═ 200/1) to give the products 3j (57.0mg, 37%) and 3j' (27.7mg, 18%) as white solids. Characterization data for compound 3j are as follows:1H NMR(400MHz,DMSO-d6)δ:1.65(s,6H),8.02(dd,J1＝8.8Hz,J2＝2.0Hz,1H),8.19(d,J＝8.8Hz,1H),8.29(d,J＝2.0Hz,1H),12.91(s,1H).13C NMR(100MHz,DMSO-d6)δ:24.5,81.1,97.3,120.2,124.3,126.2,129.9,130.6,136.5,161.8,163.5,166.8.HRMS calcd for C13H10BrNO3Na:329.9736[M+Na]+329.9743, found. Characterization data for compound 3j' are as follows:1H NMR(400MHz,DMSO-d6)δ:1.64(s,6H),7.50(t,J＝7.6Hz,1H),8.11(dd,J1＝8.0Hz,J2＝1.2Hz,1H),8.32(dd,J1＝7.6Hz,J2＝1.2Hz,1H),12.92(s,1H).13C NMR(100MHz,DMSO-d6)δ:24.8,78.8,97.3,116.5,127.6,128.1,128.5,132.3,140.2,162.1,164.1,165.3.HRMS calcd for C13H10BrNO3Na:329.9736[M+Na]+,found:329.9744。
example 26
A15 mL reaction tube was charged with 1k (82.6mg,0.5mmol), DME (3mL), and ethyl 4-hydroxy-4-methyl-2-pentynoate (2a, 1)56.2mg,1.0mmol)、[RhCp*Cl2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give product 3k as a white solid (36.5mg, 30%). The characterization data for this compound are as follows:1H NMR(600MHz,DMSO-d6)δ:1.59(s,6H),2.77(s,3H),7.33(s,1H),7.66(s,1H),8.18(s,1H),12.47(s,1H).13C NMR(150MHz,DMSO-d6)δ:23.8,25.1,80.8,97.7,120.6,123.2,130.9,133.6,133.8,142.3,163.7,164.4,167.8.HRMS calcd for C14H13NO3Na:266.0788[M+Na]+,found:266.0789。
example 27
To a 15mL reaction tube were added 1l (90.6mg,0.5mmol), DME (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp. multidot. Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor on silica gel, and separating on silica gel column (dichloromethane/methanol-200/1) to obtain 3l (44.1mg, 34%) of the product as a white solid. The characterization data for this compound are as follows:1H NMR(400MHz,DMSO-d6)δ:1.60(s,6H),3.87(s,3H),7.10(d,J＝8.4Hz,1H),7.73(t,J＝7.6Hz,1H),7.87(d,J＝7.6Hz,1H),12.39(br s,1H).13C NMR(100MHz,DMSO-d6)δ:24.5,55.8,80.1,96.4,109.9,113.2,113.6,134.4,134.9,161.0,161.1,163.7,167.2.HRMS calcd for C14H13NO4Na:282.0737[M+Na]+,found:282.0738。
example 28
At 15mLTo the reaction tube were added 1a (75.6mg,0.5mmol), DME (3mL), 2b (184.2mg,1.0mmol) and [ RhCp. multidot. Cl ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), the mixture was stirred at 100 ℃ for 12h under a nitrogen atmosphere and then cooled to room temperature. Suction filtration and spin drying of the mother liquor with silica gel and separation on silica gel (dichloromethane/methanol: 200/1) gave the product as a white solid 3m (100.3mg, 78%). The characterization data for this compound are as follows:1H NMR(400MHz,CDCl3)δ:0.88(t,J＝7.2Hz,6H),2.18-2.31(m,4H),7.64-7.68(m,1H),7.87-7.91(m,1H),8.47(d,J＝8.0Hz,1H),8.58(d,J＝8.0Hz,1H),13.29(s,1H).13C NMR(100MHz,CDCl3)δ:7.4,29.8,86.9,103.1,123.4,124.2,128.0,128.2,132.2,134.6,159.0,166.2,168.4.HRMS calcd for C15H15NO3Na:280.0944[M+Na]+,found:280.0948。
example 29
A15 mL reaction tube was charged with 1a (75.6mg,0.5mmol), DME (3mL), 2c (184.2mg,1.0mmol) and [ RhCp. Cl ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give the product 3n as a white solid (77.2mg, 60%). The characterization data for this compound are as follows:1H NMR(600MHz,CDCl3)δ:0.93(t,J＝6.6Hz,3H),1.19-1.21(m,1H),1.47-1.49(m,1H),1.85(s,3H),2.12-2.22(m,2H),7.65(t,J＝7.2Hz,1H),7.88(t,J＝7.2Hz,1H),8.47(d,J＝7.8Hz,1H),8.55(d,J＝7.8Hz,1H),13.28(s,1H).13C NMR(100MHz,CDCl3)δ:13.9,16.7,24.3,39.8,83.7,101.5,123.4,124.2,128.0,128.2,132.4,134.7,160.9,166.2,168.0.HRMS calcd for C15H15NO3Na:280.0944[M+Na]+,found:280.0944。
example 30
A15 mL reaction tube was charged with 1a (75.6mg,0.5mmol), DME (3mL), 2d (198.3mg,1.0mmol) and [ RhCp. multidot. Cl ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), the mixture was stirred at 100 ℃ under nitrogen for 12h, then cooled to room temperature, filtered with suction, the mother liquor was spin-dried over silica gel and isolated on silica gel column (dichloromethane/methanol ═ 200/1) to give product 3o as a white solid (88.2mg, 65%). The characterization data for this compound are as follows:1H NMR(600MHz,CDCl3)δ:0.83(d,J＝6.6Hz,3H),0.99(d,J＝7.2Hz,3H),1.70-1.76(m,1H),1.82(s,3H),2.03-2.07(m,1H),2.18-2.21(m,1H),7.65(t,J＝7.8Hz,1H),7.88(t,J＝7.8Hz,1H),8.46(d,J＝7.8Hz,1H),8.57(d,J＝7.8Hz,1H),13.26(s,1H).13C NMR(100MHz,CDCl3)δ:23.6,24.2,24.3,25.1,46.0,83.7,101.6,123.5,124.2,128.0,128.1,132.4,134.7,161.2,166.2,167.9.HRMS calcd for C16H17NO3Na:294.1101[M+Na]+,found:294.1102。
example 31
A15 mL reaction tube was charged with 1a (75.6mg,0.5mmol), DME (3mL), 2e (198.3mg,1.0mmol) and [ RhCp. multidot. Cl ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give the product 3p as a white solid (51.5mg, 38%). The characterization data for this compound are as follows:1H NMR(400MHz,DMSO-d6)δ:0.96(s,9H),1.64(s,3H),7.58-7.62(m,1H),7.84-7.88(m,1H),8.24(d,J＝7.6Hz,1H),8.32(d,J＝8.0Hz,1H),12.39(s,1H).13C NMR(100MHz,DMSO-d6)δ:18.3,25.1,37.6,87.7,99.4,122.1,124.4,127.6,127.8,131.3,133.9,161.5,162.9,167.6.HRMS calcd for C16H17NO3Na:294.1101[M+Na]+,found:294.1101。
example 32
A15 mL reaction tube was charged with 1a (75.6mg,0.5mmol), DME (3mL), 2f (218.2mg,1.0mmol) and [ RhCp. Cl ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor on silica gel, and separating on silica gel column (dichloromethane/methanol-200/1) to obtain 3q (23.3mg, 16%) of product as a white solid. The characterization data for this compound are as follows:1H NMR(400MHz,DMSO-d6)δ:2.10(s,3H),7.38-7.46(m,3H),7.49-7.52(m,2H),7.59-7.63(m,1H),7.85-7.89(m,1H),8.23(d,J＝7.6Hz,1H),8.35(d,J＝7.6Hz,1H),12.73(s,1H).13C NMR(100MHz,DMSO-d6)δ:22.7,83.0,97.9,122.3,124.7,125.8,127.7,127.8,128.8,129.0,131.3,133.9,137.8,162.2,162.9,167.4.HRMS calcd for C18H14NO3:292.0968[M+H]+,found:292.0973。
example 33
A15 mL reaction tube was charged with 1a (75.6mg,0.5mmol), DME (3mL), 2g (142.2mg,1.0mmol) and [ RhCp. Cl ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (95.1mg, 83%).
Example 34
A15 mL reaction tube was charged with 1a (75.6mg,0.5mmol), DME (3mL), 2h (184.2mg,1.0mmol) and [ RhCp. Cl ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating on silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (94.0mg, 82%).
Example 35
To a 15mL reaction tube were added 1m (82.6mg,0.5mmol), DME (3mL), ethyl 4-hydroxy-4-methyl-2-pentynoate (2a,156.2mg,1.0mmol) and [ RhCp. multidot. Cl [ ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give product 3a as a white solid (97.4mg, 85%).
Example 36
A15 mL reaction tube was charged with 1a (75.6mg,0.5mmol), DME (3mL), 4a (168.2mg,1.0mmol) and [ RhCp. Cl ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating through silica gel column (dichloromethane/methanol ═ 200/1) to give product 5a as a white solid (83.0mg, 65%). The characterization data for this compound are as follows:1H NMR(400MHz,DMSO-d6)δ:1.90(s,6H),2.24-2.26(m,2H),7.53(t,J＝7.2Hz,1H),7.78(t,J＝7.2Hz,1H),8.16-8.21(m,2H),12.67(br s,1H).13C NMR(100MHz,DMSO-d6)δ:24.5,37.0,90.4,98.8,121.9,124.6,127.4,127.8,131.4,133.8,160.5,163.0,167.1.HRMS calcd for C15H13NO3Na:278.0788[M+Na]+,found:278.0788。
example 37
A15 mL reaction tube was charged with 1a (75.6mg,0.5mmol), DME (3mL), 4b (182.2mg,1.0mmol) and [ RhCp. Cl ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), the mixture was stirred at 100 ℃ for 12h under a nitrogen atmosphere and then cooled to room temperature. Suction filtration and spin drying of the mother liquor with silica gel and separation on silica gel (dichloromethane/methanol-200/1) gave product 5b as a white solid (96.9mg, 72%). The characterization data for this compound are as follows:1H NMR(600MHz,DMSO-d6)δ:1.18-1.22(m,1H),1.48-1.58(m,4H),1.66-1.67(m,3H),1.97-2.02(m,2H),7.50(t,J＝7.2Hz,1H),7.74-7.77(m,1H),8.14(d,J＝7.8Hz,1H),8.19(d,J＝8.4Hz,1H),12.59(s,1H).13C NMR(100MHz,CDCl3)δ:22.0,24.7,34.2,82.9,100.7,123.4,124.3,127.9,128.1,132.6,134.6,162.0,166.2,168.1.HRMS calcd for C16H15NO3Na:292.0944[M+Na]+,found:292.0948。
example 38
A15 mL reaction tube was charged with 1a (75.6mg,0.5mmol), DME (3mL), 4c (196.2mg,1.0mmol) and [ RhCp. Cl ]2]2(7.7mg,0.0125mmol) and potassium fluoride (58.1mg,1.0mmol), stirring the mixture at 100 ℃ under nitrogen for 12h, cooling to room temperature, suction filtering, spin-drying the mother liquor with silica gel, and separating on silica gel column (dichloromethane/methanol ═ 200/1) to give product 5c as a white solid (39.7mg, 28%). The characterization data for this compound are as follows:1H NMR(600MHz,DMSO-d6)δ:1.61-1.63(m,2H),1.72-1.75(m,6H),1.81-1.84(m,2H),2.17-2.22(m,2H),7.59-7.61(m,1H),7.85-7.87(m,1H),8.24(dd,J1＝7.8Hz,J2＝0.6Hz,1H),8.29(d,J＝7.8Hz,1H),12.70(s,1H).13C NMR(100MHz,DMSO-d6)δ:21.6,26.8,36.5,85.2,96.7,122.1,124.6,127.4,127.8,131.7,133.8,163.0,164.2,167.4.HRMS calcd for C17H17NO3Na:306.1101[M+Na]+,found:306.1100。
the foregoing embodiments have described the general principles, principal features and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are merely illustrative of the principles of the present invention, and that various changes and modifications may be made without departing from the scope of the principles of the present invention, and the invention is intended to be covered by the appended claims.
Claims (4)
1. A synthetic method of furanone isoquinolone compounds is characterized in that the specific synthetic process is as follows: dissolving N-alkoxy aryl formamide compounds 1 and 4-hydroxy-2-alkynoate compounds 2 in a solvent, then adding a catalyst and an additive, and stirring and reacting at 80-120 ℃ in the atmosphere of air or nitrogen to obtain furanone and isoquinolinone compounds 3, wherein the reaction equation in the synthesis method is as follows:
wherein R is1Is hydrogen, fluorine, chlorine, bromine, C1-4Straight-chain or branched alkyl, methoxy, phenyl or substituted phenyl, the substituent on the phenyl ring of the substituted phenyl is fluorine, chlorine, bromine, methyl or methoxy, R2Is phenyl or C1-4Straight or branched alkyl, R3Is phenyl or C1-4Straight or branched alkyl, R4Is C1-4Straight or branched alkyl, R5Is C1-4Linear or branched alkyl, 1, 4-dioxane, methanol, isopropanol, acetonitrile or glycol dimethyl ether as solvent, and dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer as catalyst (RhCp Cl)2]2) The additive is cesium acetate, potassium fluoride, silver acetate, sodium acetate,Potassium acetate, potassium carbonate or sodium carbonate.
2. The method of claim 1, wherein the furanone isoquinolinone compound is selected from the group consisting of: the mass ratio of the N-alkoxy aryl formamide compound 1 to the 4-hydroxy-2-alkynoate compound 2 to the catalyst to the additive is 1:1-2:0.025: 1-2.
3. A synthetic method of furanone isoquinolone compounds is characterized in that the specific synthetic process is as follows: dissolving N-alkoxy aryl formamide compounds 1 and 4-hydroxy-2-alkynoate compounds 4 in a solvent, then adding a catalyst and an additive, and stirring and reacting at 80-120 ℃ in the atmosphere of air or nitrogen to obtain furanone and isoquinolinone compounds 5, wherein the reaction equation in the synthesis method is as follows:
wherein R is1Is hydrogen, fluorine, chlorine, bromine, C1-4Straight-chain or branched alkyl, methoxy, phenyl or substituted phenyl, the substituent on the phenyl ring of the substituted phenyl is fluorine, chlorine, bromine, methyl or methoxy, R4Is C1-4Straight or branched alkyl, R5Is C1-4Straight chain or branched alkyl, n is 1, 2 or 3, the solvent is 1, 4-dioxane, methanol, isopropanol, acetonitrile or ethylene glycol dimethyl ether, and the catalyst is dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer ([ RhCp Cl)2]2) The additive is cesium acetate, potassium fluoride, silver acetate, sodium acetate, potassium carbonate or sodium carbonate.
4. The method of claim 3, wherein the furanone isoquinolinone compound is selected from the group consisting of: the mass ratio of the N-alkoxy aryl formamide compound 1 to the 4-hydroxy-2-alkynoate compound 4 to the catalyst to the additive is 1:1-2:0.025: 1-2.
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