CN119119044A - A spirocyclic pyrroloindolone derivative and preparation method thereof - Google Patents
A spirocyclic pyrroloindolone derivative and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a spiro-pyrrole-indolinone derivative and a preparation method thereof, which belong to the field of chemical synthesis, wherein a cyclic imine ylide derivative and a 2-alkenyl indole derivative are used as raw materials, a catalyst, a solvent and alkali are added for reaction for 6-24 hours, and the spiro-pyrrole-indolinone derivative is obtained through one-step efficient synthesis; the preparation method has the advantages of simple operation, fewer reaction steps, easily available raw materials, higher yield, no need of transition metal catalyst and environmental protection; provides a new path for synthesizing the compounds; the product obtained by the preparation method has high enantioselectivity and diastereoselectivity; the preparation method has wide substrate universality, has strong compatibility to substituent groups on the substrate, avoids a lengthy separation process and a purification process of intermediate compounds in the post-treatment process through one-pot one-step reaction, thereby saving time and resources and improving the yield.
Description
Technical Field
The invention relates to the field of chemical synthesis, in particular to a spiro pyrrolo-indolone derivative and a preparation method thereof.
Background
The pyrroloindolone backbone is the core building block of many important natural products and pharmaceutically active molecules, and is also the core segment of many natural alkaloids. Because of its unique structure, the compound often shows very unique pharmacological activity, and has wide application in the pharmaceutical chemistry field, such as anticancer, antidepressant and antibacterial fields. On the other hand, spiro compounds are also very valuable building blocks and important pharmacophores, widely present in many natural products and drugs and intermediates thereof. In addition, the spiro skeleton compound may have application value in photochromic material, and the spiro structure has rigidity, great number of steric hindrance groups around the spiro atom center, etc. and the spiro atom has one quaternary carbon center as one difficulty in synthesizing chemical field.
The pyrroloindolone skeleton products reported in the current literature are mainly single pyrroloindolone structures. Literature One-Pot Organocatalytic Asymmetric Synthesis of 1H-Pyrrolo[1,2a]indol-3(2H)-ones via a Michael-Hemiaminalization-Oxidation Sequence. Synlett, 2011(4), 469-472 synthesizes a pyrroloindolone structure through organoamine catalysis and PCC relay catalysis, the method adopts a chiral amine catalyst, the price is high, a PCC oxidant is required to be added for further oxidation, and the PCC oxidation post-treatment is troublesome. Literature Chemo- and Regioselective Synthesis of Functionalized 1H-imidazo[1,5-a]indol-3(2H)-ones via a Redox-Neutral Rhodium(III)-Catalyzed [4+1] Annulation between Indoles and Alkynes. Advanced Synthesis & Catalysis, 2021, 363, 18, 4380-4389 functionalizes 1H-imidazo [1,5-a ] indol-3 (2H) -ones by redox neutral rhodium (III) -catalyzed [4+1] cyclization reaction chemistry and regioselective synthesis between indoles and alkynes, but requires the use of expensive rhodium metal and harsh reaction conditions.
In summary, the current literature reports only the pyrroloindolone structural products with a single structure, but the synthesis of the pyrroloindolone skeleton with a spiro structure is not reported at present. Therefore, development of efficient synthesis of the spiro pyrroloindolone skeleton and the derivative thereof has important research value.
Disclosure of Invention
In order to solve the technical problems, the invention provides the simple, efficient and green spiro pyrroloindolone derivative and the preparation method thereof, and the preparation method has the advantages of simple reaction system, simple operation, green and mild conditions, easily available raw materials, low price, high yield, high selectivity, easy application expansion and the like, and is expected to provide a new path for efficient synthesis of the compounds.
The technical scheme adopted by the invention is as follows:
A spiro pyrroloindolone derivative has a structural general formula shown in formula 3:
,
Wherein R 1、R2、R3 in the formula 3 is independently selected from any one of hydrogen atom, alkyl, alkoxy and halogen, and EWG is any one of nitro, ester group and carbonyl.
Further, the structural general formula of the spiro pyrroloindolone derivative is selected from any one of the following structures:
。
The preparation method of the spiro-pyrrolo-indolone derivative comprises the following steps of taking a cyclic imine ylide derivative shown in a formula 1 and a 2-alkenyl indole derivative shown in a formula 2 as raw materials, adding a catalyst, a solvent and alkali, reacting for 6-24 hours, purifying a product to obtain the spiro-pyrrolo-indolone derivative shown in a formula 3, and synthesizing a general formula shown in the specification:
;
Wherein R 1、R2、R3 in the formula 1, the formula 2 and the formula 3 is independently selected from any one of hydrogen atom, alkyl, alkoxy and halogen, and EWG is any one of nitro, ester group and carbonyl.
Preferably, the catalyst is a phase transfer catalyst or/and a metal catalyst.
Preferably, the phase transfer catalyst comprises at least one of a quaternary ammonium salt phase transfer catalyst, a quaternary phosphonium salt phase transfer catalyst, a crown ether catalyst and chiral quaternary ammonium salt or quaternary phosphonium salt catalysts thereof.
Preferably, the metal catalyst is at least one of a cupric salt (CuBr 2、CuCl2、CuI2、Cu(OAc)2、Cu(OTf)2), a cupric salt (CuBr, cuCl, cuI), a ferric salt (FeCl 3), a ferrous salt (FeCl 2、FeBr2), a cupric salt (NiBr 2、NiCl2) and a cupric salt (CoBr 2、CoCl2 、Co(OAc)2).
Preferably, the base is one of cesium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, cesium hydroxide, anhydrous potassium phosphate, potassium phosphate trihydrate, potassium phosphate heptahydrate, potassium bicarbonate.
Preferably, the solvent is at least one of toluene, benzene, tetrahydrofuran, diethyl ether, petroleum ether, n-hexane, dichloromethane, chloroform, ethyl acetate and acetonitrile.
Preferably, the molar ratio of the cyclic imine ylide derivative to the 2-alkenyl indole derivative is 1-3:1-2, the catalyst is 0.01-0.5 of the cyclic imine ylide derivative, and the alkali is 1.0-5.0 times of the cyclic imine ylide derivative.
Based on a general inventive concept, the present invention also provides a spiro pyrrolo-indolone derivative or a stereoisomer thereof.
The preparation method of the spiro pyrroloindolone derivative comprises the following steps of (as shown in figure 1), deprotonating a cyclic imine ylide derivative (substrate A) under the action of a catalyst and alkali to obtain an intermediate 1, then, attacking a double bond of a 2-alkenyl indole derivative (substrate B) by negative ions to obtain an intermediate 2, further, deprotonating under the action of alkali to form an intermediate 3, attacking an ester group by N negative ions of the intermediate 3, and leaving by methoxy to obtain a target spiro product.
Compared with the prior art, the invention has the following beneficial effects:
According to the method, the cyclic imine ylide derivative and the 2-alkenyl indole derivative are used as raw materials, the catalyst, the solvent and the alkali are added for reaction for 6-24 hours, and the spiro pyrroloindolone and the derivative thereof are obtained through one-step efficient synthesis. Provides a new path for synthesizing the compounds and has high reaction yield.
The invention has wide substrate universality, strong compatibility to substituent groups on the substrate, avoids a lengthy separation process and a purification process of intermediate compounds in the post-treatment process through one-pot one-step reaction, thereby saving time and resources and improving the yield.
The target product of the invention has novel structure, the reaction is suitable for water and air atmosphere, the product is easy to separate, and the invention is suitable for industrial production.
Drawings
FIG. 1 is a schematic diagram of the reaction of the present invention;
FIG. 2 is a nuclear magnetic resonance spectrum of the product obtained in example 2;
FIG. 3 is a nuclear magnetic resonance spectrum of the product obtained in example 2;
FIG. 4 is a nuclear magnetic resonance spectrum of the product obtained in example 26;
FIG. 5 is a nuclear magnetic resonance spectrum of the product obtained in example 26.
Detailed Description
In order to make the technical problems, technical solutions and advantages to be solved more apparent, the following detailed description will be given with reference to the accompanying drawings and specific embodiments.
The following examples are illustrative of the invention and are not intended to limit the scope of the invention. Modifications and substitutions to methods, procedures, or conditions of the present invention without departing from the spirit and nature of the invention are intended to be within the scope of the present invention.
The technical means used in the examples are conventional means known to those skilled in the art, unless otherwise indicated, and the reagents used in the examples are all commercially available, unless otherwise indicated.
Examples 1-25 preparation of Spiropyrrooindolone derivatives
Adding 0.1-0.3 mmol of cyclic imine ylide derivative (substrate A), 0.1-0.2 mmol of indole olefin derivative (substrate B), a catalyst, alkali 0.2-mmol and 10mL solvent into a reaction bottle of 25 mL in sequence, reacting for 6-24 hours at room temperature, directly post-treating after the reaction, and separating by column chromatography, wherein the reaction formula is as follows:
;
After the reaction, the product was worked up, isolated and weighed to calculate the product yield, and the catalyst, solvent and base are shown in Table 1 below.
TABLE 1 catalysts, solvents, bases, temperature times and yields of the products of examples 1-25
The products obtained in example 2 are typically represented by nuclear magnetic hydrogen spectra and nuclear magnetic carbon spectra respectively shown in fig. 2 and 3, and the products obtained in example 1 and examples 3 to 25 can obtain substantially consistent characterization results, and the product characterization data of the products obtained in example 2 are obtained by combining ：1H NMR (400 MHz, CDCl3) δ 8.06 (d, J = 7.2 Hz, 1H), 7.76 (d, J = 7.2 Hz, 2H), 7.55 (dd, J = 14.2, 7.2 Hz, 2H), 7.46–7.38 (m, 3H), 7.37–7.30 (m, 2H), 7.26 (td, J = 7.2, 1.5 Hz, 2H), 7.19 (d, J = 7.2 Hz, 1H), 6.22 (d, J = 0.6 Hz, 1H), 4.10 (ddd, J = 9.5, 4.5, 1.3 Hz, 1H), 3.49 (d, J = 16.4 Hz, 1H), 3.28 (dd, J = 17.2, 9.6 Hz, 1H), 3.17 (dd, J = 17.2, 4.7 Hz, 1H), 3.07 (d, J = 16.5 Hz, 1H), 2.48 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 196.57, 172.18, 165.55, 143.72, 136.33, 135.11, 133.56, 133.45, 131.72, 130.80, 129.15, 128.67, 127.94, 127.84, 127.77, 126.07, 124.32, 123.76, 120.85, 114.11, 102.33, 71.55, 40.92, 40.57, 29.72, 23.35. HRMS (ESI) m/z calcd for C28H22N2O2 [M+H]+ = 419.1760, found = 419.1766. with the nuclear magnetic hydrogen spectra (shown in fig. 2) and the carbon spectra (shown in fig. 3) as follows, so that the structural formula of the target product is correct.
EXAMPLE 26 preparation of Spiropyrrooindolone derivatives
To a reaction flask of 25 mL were added in order 0.12 of a cyclic imine ylide derivative of mmol, 0.12 of a mmol indolealkene derivative, 0.01 mmol of catalyst (tetrabutylammonium bromide), 0.2 of base (cesium carbonate) mmol and 10 mL of solvent (ethanol). The reaction is carried out at room temperature, the reaction is 12h, the post treatment is carried out directly after the reaction for column chromatography separation, and the reaction formula is as follows:
;
after the reaction, the product is post-treated, separated, and the product yield is calculated by weighing, and the characteristic data of the reaction product is ：1H NMR (400 MHz, CDCl3) δ 8.06 (d, J = 7.4 Hz, 1H), 7.66 (d, J = 8.2 Hz, 2H), 7.57 (d, J = 7.4 Hz, 1H), 7.44 (dd, J = 6.7, 1.6 Hz, 1H), 7.37 (dd, J = 7.5, 1.2 Hz, 1H), 7.32 (dd, J = 7.5, 1.2 Hz, 1H), 7.30 – 7.23 (m, 3H), 7.21 (d, J = 8.2 Hz, 3H), 6.21 (s, 1H), 4.08 (dd, J = 9.8, 4.5 Hz, 1H), 3.48 (d, J = 16.4 Hz, 1H), 3.25 (dd, J = 17.0, 9.8 Hz, 1H), 3.13 (dd, J = 17.0, 4.6 Hz, 1H), 3.06 (d, J = 16.5 Hz, 1H), 2.48 (s, 3H), 2.39 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 196.24, 172.21, 165.50, 144.34, 143.81, 135.13, 133.92, 133.63, 131.69, 130.79, 129.34, 129.15, 128.07, 127.84, 127.74, 126.04, 124.29, 123.72, 120.84, 114.10, 102.33, 71.57, 41.02, 40.47, 29.69, 23.35, 21.66. HRMS (ESI) m/z calcd for C29H24N2O2 [M+H]+ = 433.1916, found = 433.1918. combined with nuclear magnetic hydrogen spectrum (shown in figure 4) and carbon spectrum (shown in figure 5), so that the structural formula of the target product is correct.
EXAMPLE 27 preparation of Spiropyrrooindolone derivatives
To a reaction flask of 25 mL was added 0.12 of a cyclic imine ylide derivative of mmol, 0.15 of a mmol indolealkene derivative, 0.01mmol of catalyst (tetrabutylammonium bromide), 0.2 of base (cesium carbonate) mmol and 10 mL of solvent (ethanol) in this order. The reaction is carried out at room temperature, the reaction is 12h, the post treatment is carried out directly after the reaction for column chromatography separation, and the reaction formula is as follows:
;
after the reaction, the product is post-treated, separated, and the product yield is calculated by weighing, and the characterization data of the reaction product is shown as ：1H NMR (400 MHz, CDCl3) δ 8.05 (d, J = 7.4 Hz, 1H), 7.62 (d, J = 8.2 Hz, 2H), 7.53 (d, J = 7.2 Hz, 1H), 7.44 (dd, J = 6.7, 1.6 Hz, 1H), 7.37 (dd, J = 7.5, 1.2 Hz, 1H), 7.32 (dd, J = 7.5, 1.2 Hz, 1H), 7.30 – 7.23 (m, 3H), 7.21 (d, J = 8.2 Hz, 3H), 6.21 (s, 1H), 4.08 (dd, J = 9.8, 4.5 Hz, 1H), 3.48 (d, J = 16.4 Hz, 1H), 3.25 (dd, J = 17.0, 9.8 Hz, 1H), 3.13 (dd, J = 17.0, 4.6 Hz, 1H), 3.06 (d, J = 16.5 Hz, 1H), 2.48 (s, 3H), 2.39 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 196.20, 172.22, 165.30, 144.34, 143.81, 135.13, 133.92, 133.63, 131.69, 130.79, 129.34, 129.10, 128.17, 127.84, 127.74, 126.04, 124.29, 123.72, 120.84, 114.20, 102.32, 71.54, 41.02, 40.42, 29.69, 23.31, 21.60. HRMS (ESI) m/z calcd for C29H24N2O2 [M+H]+ = 433.1916, found = 433.1918. , so that the structural formula of the target product is correct.
EXAMPLE 28 preparation of Spiropyrrooindolone derivatives
To a reaction flask of 25 mL was added in order 0.12 of a cyclic imine ylide derivative of mmol, 0.1mmol of a 4-chloro substituted indolealkene derivative, 0.01mmol of catalyst (tetrabutylammonium bromide), 0.2 of base (cesium carbonate) mmol and 10mL of solvent (ethanol). The reaction is carried out at room temperature, the reaction is 12h, the post treatment is carried out directly after the reaction for column chromatography separation, and the reaction formula is as follows:
;
The product characterization data is shown below ：1H NMR (400 MHz, CDCl3) δ 8.10 (d, J = 7.2 Hz, 1H), 7.73 (d, J = 7.2 Hz, 2H), 7.43 (dd, J = 14.2, 7.2 Hz, 2H), 7.56–7.32 (m, 2H), 7.37–7.31 (m, 2H), 7.26 (td, J = 7.2, 1.5 Hz, 2H), 7.19 (d, J = 7.2 Hz, 1H), 6.22 (d, J = 0.6 Hz, 1H), 4.10 (ddd, J = 9.5, 4.5, 1.3 Hz, 1H), 3.49 (d, J = 16.4 Hz, 1H), 3.28 (dd, J = 17.2, 9.6 Hz, 1H), 3.17 (dd, J = 17.2, 4.7 Hz, 1H), 3.07 (d, J = 16.5 Hz, 1H), 2.48 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 196.67, 172.30, 165.22, 143.42, 136.33, 135.31, 133.56, 132.45, 131.70, 130.81, 129.15, 128.57, 127.94, 127.84, 127.77, 126.07, 124.32, 123.76, 120.85, 114.21, 102.33, 71.55, 40.92, 40.47, 29.42, 23.32. HRMS (ESI) m/z calcd for C28H21ClN2O2 [M+H]+ = 453.1370, found = 453.1365. , and the structural formula of the target product is correct.
The above description is only a preferred embodiment of the present invention, and the scope of the present invention is not limited to the above examples. Modifications and variations which would be obvious to those skilled in the art without departing from the technical spirit of the present invention are also considered to be within the scope of the present invention.
Claims (10)
1. The spiro-pyrrolo-indolone derivative is characterized by having a structural general formula shown in formula 3:
,
Wherein R 1、R2、R3 in the formula 3 is independently selected from any one of hydrogen atom, alkyl, alkoxy and halogen, and EWG is any one of nitro, ester group and carbonyl.
2. The spirocyclic pyrroloindolone derivative according to claim 1, characterized in that the structural general formula of the spirocyclic pyrroloindolone derivative is selected from any one of the following structures:
。
3. The preparation method of the spiro-pyrrolo-indolone derivative according to claim 1 or 2 is characterized by comprising the following steps of taking a cyclic imine ylide derivative shown in formula 1 and a 2-alkenyl indole derivative shown in formula 2 as raw materials, adding a catalyst, a solvent and alkali, reacting for 6-24 hours, and purifying a product to obtain the spiro-pyrrolo-indolone derivative shown in formula 3, wherein the synthetic general formula is shown as follows:
;
Wherein R 1、R2、R3 in the formula 1, the formula 2 and the formula 3 is independently selected from any one of hydrogen atom, alkyl, alkoxy and halogen, and EWG is any one of nitro, ester group and carbonyl.
4. A process according to claim 3, wherein the catalyst is a phase transfer catalyst or/and a metal catalyst.
5. The method according to claim 4, wherein the phase transfer catalyst is at least one of a quaternary ammonium salt phase transfer catalyst, a quaternary phosphonium salt phase transfer catalyst, a crown ether catalyst, and chiral quaternary ammonium salt or quaternary phosphonium salt catalyst thereof, and the metal catalyst is at least one of a cupric salt, a ferric salt, a ferrous salt, a divalent nickel salt, and a divalent cobalt salt.
6. The method according to claim 4, wherein the divalent copper salt is at least one of CuBr 2、CuCl2、CuI2、Cu(OAc)2、Cu(OTf)2, the monovalent copper salt is at least one of CuBr, cuCl, cuI, the trivalent iron salt is FeCl 3, the divalent iron salt is at least one of FeCl 2、FeBr2, the divalent nickel salt is at least one of NiBr 2、NiCl2, and the divalent cobalt salt is at least one of CoBr 2、CoCl2 、Co(OAc)2.
7. The method according to claim 3, wherein the base is one of cesium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, cesium hydroxide, anhydrous potassium phosphate, potassium phosphate trihydrate, potassium phosphate heptahydrate, and potassium bicarbonate.
8. The method according to claim 3, wherein the solvent is at least one of toluene, benzene, tetrahydrofuran, diethyl ether, petroleum ether, n-hexane, methylene chloride, chloroform, ethyl acetate, and acetonitrile.
9. The preparation method according to claim 3, wherein the molar ratio of the cyclic imine ylide derivative to the 2-alkenylindole derivative is 1-3:1-2, the catalyst is 0.01-0.5 of the molar amount of the cyclic imine ylide derivative, and the alkali is 1.0-5.0 times of the molar amount of the cyclic imine ylide derivative.
10. A spiro-pyrrolo-indolone derivative according to claim 1 or 2 or a stereoisomer of a spiro-pyrrolo-indolone derivative obtainable by the process of any one of claims 3 to 9.
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| CN108976238A (en) * | 2018-08-27 | 2018-12-11 | 广西中医药大学 | 4 ' of one kind, the chiral method for preparing of the double loop coil Oxoindole compounds of 5 '-bis trifluoromethyl -3,3 '-pyrrolidinyl |
| CN116199614A (en) * | 2023-02-03 | 2023-06-02 | 江苏师范大学 | A kind of N-N axis chiral indole-pyrrole compound and its synthesis method |
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