Spirocyclic propane-oxidized indole compounds and methods for preparing the same

Abstract

This invention discloses a spirocyclopropane-oxidized indole compound and its preparation method, comprising the following steps: S1, dissolving dicyano-substituted 3-methylene indole and benzoyl carbamate compounds in an organic solvent to obtain a reaction mixture; S2, adding tris(dimethylamino)phosphine to the reaction mixture to construct a one-pot reaction system; S3, carrying out a one-pot stirred reaction at room temperature, and obtaining the spirocyclopropane-oxidized indole product after separation and purification after the reaction is complete. This invention solves the technical problems of existing spirocyclopropane-oxidized indole synthesis processes, such as the need for ultra-low temperature pre-reaction, cumbersome operation, and poor diastereoselectivity. Furthermore, the novel dicyano-substituted spirocyclopropane-oxidized indole compound synthesized by this invention possesses both the conformational restriction structure of cyclopropane and the advantageous pharmacodynamic skeleton of spirocyclopropane-oxidized indole, providing new candidate molecular structures for drug development in the fields of antitumor, anti-inflammatory, and antiviral applications, and showing promising application prospects.

Description

Technical Field

[0001] This invention relates to a spirocyclopropane-oxidized indole compound and its preparation method, belonging to the fields of organic synthesis and medicinal chemistry. Background Technology

[0002] Cyclopropanes are ubiquitous structural units with multifunctional influences in pharmaceuticals, agrochemicals, and numerous bioactive natural products. Because cyclopropanes can effectively restrict conformation without altering the chemical and physical properties of compounds, they hold significant value in the pharmaceutical field. On the other hand, the spirocyclopropyl indole skeleton has always been a synthetically challenging molecular skeleton with unique structural advantages, widely found in many drugs and bioactive natural products. In particular, the spirocyclopropyl indole core, as a compelling pharmacophore in drug discovery chemistry, has attracted considerable synthetic interest.

[0003] Currently, the synthesis of spirocyclopropane indole involves using 3-arylmethylene indole as a substrate, which undergoes a [2+1] cyclization reaction with methyl benzoylformate in the presence of phosphine (P(NMe2)3) to prepare the target product. The specific operational procedure is as follows: first, methyl benzoylformate and P(NMe2)3 are subjected to a pre-reaction at -78℃. After the pre-reaction is complete, the system is restored to room temperature, and then 3-arylmethylene indole is added for the subsequent cyclization reaction. The final product is a mixture of three diastereomers.

[0004]

[0005] However, the existing process suffers from poor reactivity and spatial configuration matching between the 3-arylmethylene oxyindole substrate and the reaction system. Firstly, the double bond reactivity of this substrate is low. To avoid side reactions and deactivation of the reactive intermediate formed by P(NMe2)3 and methyl benzoate at room temperature, pre-reaction at -78°C and stepwise feeding are necessary. This necessitates high dependence on cryogenic refrigeration equipment, high energy consumption, and cumbersome operation, significantly increasing hardware and operating costs for industrial-scale production. Secondly, the steric hindrance of the 3-position substituted aryl group in this substrate prevents effective control of the stereoorientation of the cyclization reaction. Multiple transition states with various spatial configurations can be generated during cyclization, leading to various diastereomeric products. Therefore, the existing process faces the technical challenge of achieving highly diastereoselective synthesis of spirocyclopropane oxyindole under mild reaction conditions. Furthermore, the three diastereomers obtained by existing processes have similar physicochemical properties, and the subsequent separation and purification processes are complex, with large separation losses and low atom economy. The resulting products are difficult to meet the high purity requirements of single-configuration compounds in drug synthesis. Summary of the Invention

[0006] (a) Purpose of the invention

[0007] One objective of this invention is to provide a novel class of spirocyclopropane-oxidized indole compounds, offering new structural options for the development of bioactive molecules and drugs. Another objective of this invention is to provide a method for preparing such spirocyclopropane-oxidized indole compounds, thereby solving the technical problems of existing spirocyclopropane-oxidized indole synthesis processes, which require ultra-low temperature pre-reaction, are cumbersome to operate, and have poor diastereoselectivity.

[0008] (II) Technical Solution

[0009] In a first aspect, the present invention provides a spirocyclopropane-1,3'-oxoindole compound having a spiro[cyclopropane-1,3'-oxoindole] core structure, wherein the cyclopropane ring of the core has two cyano substitutions, and the compound satisfies the following general formula:

[0010]

[0011] In the general formula:

[0012] R1 is a substituent at the benzene ring position of the indole nucleus, independently selected from hydrogen, halogen, C1-C3 alkyl, and C1-C3 alkoxy.

[0013] R2 is a substituent at the N atom position of the indole oxidized core, independently selected from C1-C3 alkyl groups;

[0014] R3 is a substituent at the benzoylbenzene ring position, independently selected from hydrogen, halogen, and C1-C3 alkyl groups.

[0015] Preferably, R1 is independently selected from hydrogen, fluorine, chlorine, bromine, methyl, and methoxy.

[0016] Preferably, R2 is methyl.

[0017] Preferably, R3 is independently selected from hydrogen, fluorine, chlorine, bromine, and methyl.

[0018] Preferably, the compound is any one of the following:

[0019] , , , , , , or .

[0020] Secondly, the present invention provides a method for preparing spirocyclopropane-oxidized indole compounds, comprising the following steps:

[0021] S1. Dissolve dicyano-substituted 3-methylene indole and benzoyl carbamate compounds in an organic solvent to obtain a mixture of reaction raw materials;

[0022] S2. Add tris(dimethylamino)phosphine to the reaction mixture to construct a one-pot reaction system;

[0023] S3. A one-pot stirred reaction was carried out at room temperature. After the reaction was complete, the product was obtained by separation and purification.

[0024] Preferably, in step S1, the organic solvent is selected from any one of toluene, methyl tert-butyl ether, and acetone.

[0025] Preferably, in step S1, the benzoyl carbamate compound is ethyl benzoyl carbamate.

[0026] Preferably, in step S3, the stirring reaction lasts for 8 to 15 hours.

[0027] Preferably, in step S3, the separation and purification are performed using column chromatography, and the eluent is a mixture of petroleum ether and ethyl acetate with a volume ratio of 3 to 8:1.

[0028] (III) Beneficial Effects

[0029] Compared with the prior art, the present invention has the following main advantages:

[0030] First, the reaction conditions are mild, the operation is simple, and the production cost is low. This invention uses dicyano-substituted 3-methylene indole oxide as the reaction substrate. The double bond of this substrate has higher reactivity, eliminating the need for pre-reaction of tris(dimethylamino)phosphine and benzoyl carbamate compounds at -78℃ ultra-low temperature conditions. The entire reaction process can be completed directly at room temperature using a one-pot method, without the need for ultra-low temperature refrigeration equipment. This significantly reduces reaction energy consumption and hardware investment costs, while also eliminating the cumbersome pre-reaction and step-by-step feeding procedures, making it more suitable for industrial-scale production.

[0031] Second, it exhibits high diastereoselectivity, yields a single product, and boasts high synthetic efficiency. The cyano substituent of the dicyano-substituted 3-methylene oxyindole substrate possesses a strong electron-withdrawing effect and suitable steric hindrance, enabling precise control of the stereoorientation of the cyclization reaction. Combined with the reaction system constructed from tris(dimethylamino)phosphine and benzoyl carbamate compounds, it can achieve highly diastereoselective spirocyclopropanation reactions, yielding only a single diastereomeric target product. This avoids the complex subsequent separation and purification steps of multiple isomers in existing technologies, reducing separation losses and significantly improving the atom economy and synthetic efficiency of the reaction. The purity of the obtained product can directly meet the high-purity requirements of drug synthesis.

[0032] Furthermore, the novel dicyano-substituted spirocyclopropane-oxidized indole compounds synthesized in this invention possess both the conformational restriction structure of cyclopropane and the advantageous pharmacological skeleton of spirocyclopropane-oxidized indole, which can provide new candidate molecular structures for drug development in the fields of antitumor, anti-inflammatory, and antiviral, and have good application prospects. Attached Figure Description

[0033] Figure 1 The hydrogen spectrum of Ⅲ-h obtained in Example 8;

[0034] Figure 2 The carbon spectrum of Ⅲ-h obtained in Example 8;

[0035] Figure 3 This is a single crystal image of Ⅲ-h obtained in Example 8. Detailed Implementation

[0036] To make the above-mentioned objects, features, and advantages of the present invention more apparent and understandable, specific embodiments of the present invention will be described in detail below with reference to the accompanying drawings. Many specific details are set forth in the following description to provide a thorough understanding of the present invention. However, the present invention can be practiced in many other ways different from those described herein, and those skilled in the art can make similar modifications without departing from the spirit of the present invention. Therefore, the present invention is not limited to the specific embodiments disclosed below.

[0037] This invention utilizes dicyano-substituted 3-methylene oxide indole as the reaction substrate, leveraging the strong electron-withdrawing effect of the cyano group to enhance the reactivity of the substrate's double bond. It enables a one-pot synthesis by allowing the substrate to undergo a [2+1] cyclization reaction with a reaction system composed of tris(dimethylamino)phosphine and benzoyl carbamate compounds at room temperature without the need for ultra-low temperature pre-reaction. Simultaneously, the steric hindrance effect of the cyano group is used to regulate the stereoorientation of the cyclization reaction, achieving high diastereoselectivity and yielding only the target product with a single configuration. This fundamentally solves the problems existing in current processes.

[0038] Referring to the following reaction formula, 3-methylene indole oxide (I) and ethyl benzoylformate (II) were dissolved in an organic solvent, and then tris(dimethylamino)phosphine was added. The mixture was stirred at room temperature (20~25℃) for 8~15 hours. After the reaction was complete, the product (III) of spirocyclopropane indole oxide was obtained by direct separation and purification by column chromatography.

[0039]

[0040] The following example illustrates the synthesis of specific indole compounds derived from spirocyclopropane oxidation:

[0041] Example 1: Synthesis of compound (Ⅲ-a)

[0042] The structural formula of compound Ⅲ-a:

[0043]

[0044] Synthesis of compound III-a:

[0045]

[0046] In a reaction tube, 3-methylene indole oxide (Ia), ethyl benzoylformate (II-a), tris(dimethylamino)phosphine and solvent were added and stirred at room temperature for 12 hours. After the reaction was complete, the crude product was purified by column chromatography (petroleum ether: ethyl acetate = 5:1) to obtain compound III-a. Different reaction conditions are shown in Table 1.

[0047]

[0048] White solid; 35.7 mg, yield 96%; mp 152.1–153.9 °C; dr > 20:1; 1 NMR (600MHz, CDCl3) δ 7.51 – 7.46 (m, 1H), 7.46 – 7.40 (m, 3H), 7.40 – 7.28 (m, 2H), 7.08 – 6.97 (m, 1H), 6.95 – 6.85 (m, 1H), 6.17 (dd, J = 7.8, 1.2 Hz, 1H),4.36 – 4.29 (m, 1H), 4.28 – 4.17 (m, 1H), 3.39 (s, 3H), 1.30 (t, J = 7.1 Hz,3H); 13 C NMR (101 MHz, CDCl3) δ 166.9, 163.6, 145.3, 131.0, 130.7, 130.5,129.3, 127.0, 126.3, 122.7, 117.9, 110.3, 109.8, 109.3, 63.7, 51.5, 45.2,27.3, 24.2, 13.7; HRMS (ESI) Calcd. for C 22 H 17 N3O3Na + (M+Na) + 394.11621, found 394.11624.

[0049] As can be seen from Table 1, using methyl ether as a solvent and reacting at room temperature for 12 hours is a more preferred approach.

[0050] Example 2: Synthesis of compound (Ⅲ-b)

[0051] The structural formula of compound Ⅲ-b:

[0052]

[0053] Synthesis of compound III-b:

[0054]

[0055] In a reaction tube, 3-methylene indole oxide (Ib), ethyl benzoylformate (II-a), tris(dimethylamino)phosphine, and tertiary methyl ether were added. The mixture was stirred at room temperature for 12 hours until the reaction was complete. The crude product was purified by column chromatography (petroleum ether:ethyl acetate = 5:1) to give compound III-b. White solid; 37.3 mg, yield 92%; mp 158.7–160.3 °C; dr > 20:1; 1 H NMR (600 MHz, CDCl3) δ 7.51 – 7.47 (m, 1H), 7.46 –7.41 (m, 2H), 7.41 – 7.27 (m, 2H), 7.04 (d, J = 1.9 Hz, 1H), 6.88 (dd, J =8.2, 1.9 Hz, 1H), 6.06 (d, J = 8.2 Hz, 1H), 4.36 – 4.27 (m, 1H), 4.27 – 4.17(m, 1H), 3.37 (s, 3H), 1.29 (t, J = 7.1 Hz, 3H); 13 C NMR (101 MHz, CDCl3) δ166.8, 163.3, 146.4, 137.3, 130.7, 130.6, 129.3, 127.0, 126.7, 122.6, 116.2,110.1, 109.4, 63.8, 51.5, 44.8, 27.4, 24.2, 13.7; HRMS (ESI) Calcd. forC 22 H 16 ClN3O3Na + (M+Na) + 428.07724, 430.07429, found 428.07751, 430.07437.

[0056] Example 3: Synthesis of compound (Ⅲ-c)

[0057] The structural formula of compound Ⅲ-c:

[0058]

[0059] Synthesis of compound III-c:

[0060]

[0061] In a reaction tube, 3-methylene indole oxide (Ic), ethyl benzoylformate (II-a), tris(dimethylamino)phosphine, and tertiary methyl ether were added. The mixture was stirred at room temperature for 12 hours until the reaction was complete. The crude product was purified by column chromatography (petroleum ether:ethyl acetate = 5:1) to give compound III-c. White solid; 42.2 mg, yield 94%; mp 165.5–167.8 °C; dr > 20:1; 1 H NMR (600 MHz, CDCl3) δ 7.51 – 7.47 (m, 1H), 7.46 –7.41 (m, 2H), 7.41 – 7.27 (m, 2H), 7.19 (d, J = 1.7 Hz, 1H), 7.05 (dd, J =8.2, 1.7 Hz, 1H), 5.99 (d, J = 8.2 Hz, 1H), 4.37 – 4.29 (m, 1H), 4.27 – 4.16(m, 1H), 3.37 (s, 3H), 1.30 (t, J = 7.1 Hz, 3H); 13 C NMR (101 MHz, CDCl3) δ166.7, 163.3, 146.4, 130.7, 130.6, 129.4, 127.2, 126.7, 125.6, 125.3, 116.7,112.9, 110.1, 109.4, 63.8, 51.5, 44.8, 27.5, 24.1, 13.7; HRMS (ESI) Calcd.for C 22 H 16 BrN3O3Na + (M+Na) + 472.02672, 474.02468, found 472.02698, 474.02487.

[0062] Example 4: Synthesis of compound (Ⅲ-d)

[0063] The structural formula of compound Ⅲ-d:

[0064]

[0065] Synthesis of compound III-d:

[0066]

[0067] In a reaction tube, 3-methylene indole oxide (Id), ethyl benzoylformate (II-a), tris(dimethylamino)phosphine, and tertiary methyl ether were added. The mixture was stirred at room temperature for 12 hours. After the reaction was complete, the crude product was purified by column chromatography (petroleum ether:ethyl acetate = 5:1) to give compound III-d. White solid; 32.5 mg, yield 81%; mp 142.8–144.8 °C; dr > 20:1; 1 H NMR (600 MHz, CDCl3) δ 7.50 – 7.45 (m, 1H), 7.44 –7.41 (m, 2H), 7.41 – 7.29 (m, 2H), 6.58 (d, J = 2.3 Hz, 1H), 6.39 (dd, J =8.6, 2.3 Hz, 1H), 6.06 (d, J = 8.5 Hz, 1H), 4.32 (dq, J = 10.7, 7.1 Hz, 1H), 4.22 (dq, J = 10.7, 7.1 Hz, 1H), 3.82 (s, 3H), 3.35 (s, 3H), 1.30 (t, J = 7.2Hz, 3H); 13 C NMR (151 MHz, CDCl3) δ 167.5, 163.7, 162.4, 146.8, 130.7, 130.4,129.2, 127.2, 127.2, 110.6, 109.9, 109.3, 106.6, 97.5, 63.6, 55.8, 51.0,45.6, 27.3, 24.0, 13.7; HRMS (ESI) Calcd. for C 23 H 19 N 3 O 4 Na + (M+Na) + 424.12677, found 424.12665.

[0068] Example 5: Synthesis of compound (Ⅲ-e)

[0069] The structural formula of compound Ⅲ-e:

[0070]

[0071] Synthesis of compound III-e:

[0072]

[0073] In a reaction tube, 3-methylene indole oxide (Ie), ethyl benzoylformate (II-a), tris(dimethylamino)phosphine, and tertiary methyl ether were added. The mixture was stirred at room temperature for 12 hours. After the reaction was complete, the crude product was purified by column chromatography (petroleum ether:ethyl acetate = 5:1) to give compound III-e. White solid; 38.2 mg, yield 85%; mp 145.7–149.2 °C; dr > 20:1; 1 H NMR (600 MHz, CDCl3) δ 7.55 – 7.50 (m, 1H), 7.49 –7.44 (m, 2H), 7.42 (dd, J = 8.4, 2.1 Hz, 1H), 7.36 (s, 2H), 6.96 (d, J = 8.4Hz, 1H), 6.10 (d, J = 2.1 Hz, 1H), 4.32 (dq, J = 10.7, 7.1 Hz, 1H), 4.23 (dq,J = 10.7, 7.1 Hz, 1H), 3.37 (s, 3H), 1.30 (t, J = 7.1 Hz, 3H); 13 C NMR (101MHz, CDCl3) δ 166.5, 163.3, 143.8, 130.9, 130.9, 130.6, 129.4, 128.3, 126.5,126.4, 119.5, 110.2, 110.0, 109.4, 63.8, 51.7, 44.7, 27.5, 24.3, 13.7; HRMS(ESI) Calcd. for C 22 H 16 BrN3O3Na + (M+Na) + 472.02672, 474.02468, found 472.02695,474.02481.

[0074] Example 6: Synthesis of compound (Ⅲ-f)

[0075] The structural formula of compound Ⅲ-f:

[0076]

[0077] Synthesis of compound III-f:

[0078]

[0079] In a reaction tube, 3-methylene indole oxide (If), ethyl benzoylformate (II-a), tris(dimethylamino)phosphine, and tertiary methyl ether were added. The mixture was stirred at room temperature for 12 hours until the reaction was complete. The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 5:1) to give compound III-f. White solid; 37.0 mg, yield 95%; mp 140.6–143.1 °C; dr > 20:1; 1 H NMR (600 MHz, CDCl3) δ 7.53 – 7.46 (m, 1H), 7.46 –7.41 (m, 2H), 7.40 – 7.27 (m, 2H), 7.21 – 7.13 (m, 1H), 6.88 – 6.81 (m, 1H), 5.94 (dd, J = 7.7, 1.0 Hz, 1H), 4.32 (dq, J = 10.7, 7.1 Hz, 1H), 4.24 (dq, J= 10.7, 7.1 Hz, 1H), 3.60 (d, J = 2.9 Hz, 3H), 1.30 (t, J = 7.1 Hz, 3H); 13 CNMR (101 MHz, CDCl3) δ 166.6, 163.4, 148.1 (d, J = 245.1 Hz), 132.2 (d, J =9.8 Hz), 130.7, 129.3, 126.7, 123.2 (d, J = 6.5 Hz), 122.2 (d, J = 3.5 Hz), 120.5, 119.0 (d, J = 19.1 Hz), 110.1, 109.5, 63.9, 51.9, 45.0, 30.0 (d, J =6.2 Hz), 24.6, 13.7; HRMS (ESI) Calcd. for C 22 H 16 FN3O3Na + (M+Na) + 412.10679, found 412.10693.

[0080] Example 7: Synthesis of compound (Ⅲ-g)

[0081] The structural formula of compound Ⅲ-g:

[0082]

[0083] Synthesis of compound III-g:

[0084]

[0085] In a reaction tube, 3-methylene indole oxide (Ia), ethyl benzoylformate (II-b), tris(dimethylamino)phosphine, and tertiary methyl ether were added. The mixture was stirred at room temperature for 12 hours until the reaction was complete. The crude product was purified by column chromatography (petroleum ether:ethyl acetate = 5:1) to give compound III-g. White solid; 36.1 mg, yield 80%; mp 157.2–159.5 °C; dr > 20:1; 1 H NMR (600 MHz, CDCl3) δ 7.57 (d, J = 8.3 Hz, 2H), 7.49– 7.43 (m, 1H), 7.35 – 7.12 (m, 2H), 7.04 (d, J = 7.9 Hz, 1H), 7.00 – 6.94(m, 1H), 6.22 (dd, J = 7.7, 1.1 Hz, 1H), 4.32 (dq, J = 10.7, 7.1 Hz, 1H), 4.24 (dq, J = 10.7, 7.1 Hz, 1H), 3.38 (s, 3H), 1.30 (t, J = 7.2 Hz, 3H); 13 CNMR (101 MHz, CDCl3) δ 166.6, 163.2, 145.3, 132.6, 132.3, 131.2, 126.0,125.3, 122.9, 117.5, 110.2, 109.5, 63.9, 50.8, 45.0, 27.4, 24.0, 13.7; HRMS(ESI) Calcd. for C 22 H 16 BrN3O3Na + (M+Na) + 472.02672, 474.02468, found 472.02704,474.02499.

[0086] Example 8: Synthesis of compound (Ⅲ-h)

[0087] The structural formula of compound Ⅲ-h:

[0088]

[0089] Synthesis of compound III-h:

[0090]

[0091] In a reaction tube, 3-methylene indole oxide (Ia), ethyl benzoylformate (II-c), tris(dimethylamino)phosphine, and tertiary methyl ether were added. The mixture was stirred at room temperature for 12 hours. After the reaction was complete, the crude product was purified by column chromatography (petroleum ether:ethyl acetate = 5:1) to give compound III-h. White solid; 37.3 mg, yield 97%; mp 135.7–138.5 °C; dr > 20:1; 1 H NMR (600 MHz, CDCl3) δ 7.47 – 7.40 (m, 1H), 7.30 –7.17 (m, 4H), 7.03 (dd, J = 8.3, 4.3 Hz, 1H), 6.96 – 6.88 (m, 1H), 6.23 (dd,J = 7.9, 4.3 Hz, 1H), 4.37 – 4.28 (m, 1H), 4.28 – 4.15 (m, 1H), 3.44 – 3.30(m, 3H), 2.45 – 2.31 (m, 3H), 1.36 – 1.25 (m, 3H); 13 C NMR (101 MHz, CDCl3) δ166.9, 163.8, 145.3, 140.8, 130.9, 130.5, 129.9, 126.3, 123.9, 122.7, 118.0,110.4, 109.9, 109.2, 63.6, 51.4, 45.2, 27.3, 24.2, 21.5, 13.7; HRMS (ESI)Calcd. for C 23 H 19 N3O3Na + (M+Na) + 408.13186 was found; 408.13187 was also found.

[0092] The proton NMR spectrum of compound III-h obtained in this embodiment is shown in [reference needed]. Figure 1 See carbon spectrum Figure 2 See the single-crystal diffraction characterization results. Figure 3 It can be seen that the product after the reaction is a single diastereomeric product, with no other isomers formed.

[0093] The embodiments described above are merely illustrative of several implementations of the present invention, and while the descriptions are specific and detailed, they should not be construed as limiting the scope of the present invention. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of the present invention, and these modifications and improvements all fall within the scope of protection of the present invention. Therefore, the scope of protection of this patent should be determined by the appended claims.

Claims

1. A spirocyclopropane-oxidized indole compound, characterized in that, The compound has a spiro[cyclopropane-1,3'-oxindole] core structure, wherein the cyclopropane ring of the core has two cyano substitutions, and the compound satisfies the following general formula: 、 In the general formula: R1 is a substituent at the benzene ring position of the indole nucleus, independently selected from hydrogen, halogen, C1-C3 alkyl, and C1-C3 alkoxy. R2 is a substituent at the N atom position of the indole oxidized core, independently selected from C1-C3 alkyl groups; R3 is a substituent at the benzoylbenzene ring position, independently selected from hydrogen, halogen, and C1-C3 alkyl groups.

2. The spirocyclopropane-oxidized indole compound according to claim 1, characterized in that, R1 is independently selected from hydrogen, fluorine, chlorine, bromine, methyl, and methoxy.

3. The spirocyclopropane-oxidized indole compound according to claim 1, characterized in that, R2 is a methyl group.

4. The spirocyclopropane-oxidized indole compound according to claim 1, characterized in that, The R3 is independently selected from hydrogen, fluorine, chlorine, bromine, and methyl.

5. The spirocyclopropane-oxidized indole compound according to claim 1, characterized in that, The compound is any one of the following: , , , , , , or .

6. A method for preparing spirocyclopropane-oxidized indole compounds, characterized in that, Includes the following steps: S1. Dissolve dicyano-substituted 3-methylene indole and benzoyl carbamate compounds in an organic solvent to obtain a mixture of reaction raw materials; S2. Add tris(dimethylamino)phosphine to the reaction mixture to construct a one-pot reaction system; S3. A one-pot stirred reaction was carried out at room temperature. After the reaction was complete, the product was obtained by separation and purification.

7. The method for preparing spirocyclopropane-oxidized indole compounds according to claim 6, characterized in that, In step S1, the organic solvent is selected from any one of toluene, methyl tert-butyl ether, and acetone.

8. The method for preparing spirocyclopropane-oxidized indole compounds according to claim 6, characterized in that, In step S1, the benzoyl carbamate compound is ethyl benzoyl carbamate.

9. The method for preparing spirocyclopropane-oxidized indole compounds according to claim 6, characterized in that, In step S3, the stirring reaction lasts for 8 to 15 hours.

10. The method for preparing spirocyclopropane-oxidized indole compounds according to claim 6, characterized in that, In step S3, the separation and purification are performed using column chromatography, with the eluent being a mixture of petroleum ether and ethyl acetate in a volume ratio of 3 to 8:1.

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