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A kind of pyrrolo[2,1-a]isoindolinone compound and its synthesis method

A synthesis method and compound technology, applied in organic chemistry and other directions, to achieve the effects of good practicability, convenient operation and low cost

Inactive Publication Date: 2019-06-07
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of cheaper and readily available N-containing organic bases to catalyze or promote this type of reaction has not been reported in the literature so far

Method used

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  • A kind of pyrrolo[2,1-a]isoindolinone compound and its synthesis method
  • A kind of pyrrolo[2,1-a]isoindolinone compound and its synthesis method
  • A kind of pyrrolo[2,1-a]isoindolinone compound and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Hydroxy-5-oxo-5,9b-hydroxy-3H-pyrrolo[2,1-a]isoindole 1,3, of 1-benzyl-3,3-diethyl-9b 3-Tricarboxylate (III-1)

[0040] In a 25 mL round bottom flask was added acetonitrile (5 mL), 2-(2-(1,3-diisoindolinonyl))-diethyl malonate (122 mg, 0.4 mmol), benzyl propiolate (128mg, 0.8mmol) and triethylamine (8mg, 0.08mmol). The reaction was stirred at 0°C for 100h. The reaction solution was concentrated, and eluted by column chromatography using a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 4:1 as the eluent to obtain 102 mg of white solid III-1 with a yield of 55%.

[0041] 1H NMR (DMSO) δ7.95 (d, J=7.5Hz, 1H), 7.73-7.55 (m, 3H), 7.55-7.30 (m, 6H), 7.16 (s, 1H), 5.41-5.25 (m, 2H), 4.47-4.01(m, 4H), 1.27(t, J=7.1Hz, 3H), 1.10(t, J=7.1Hz, 3H); HRMS (ESI + )m / z 488.1326[M+Na] + .

Embodiment 2

[0042] Example 2: 3,3-diethyl-1-(4-methylbenzyl)-9b-hydroxy-5-oxo-5,9b-dihydro-3H-pyrrolo[2,1-a] Isoindole-1,3,3-tricarboxylate (III-2)

[0043] Using II-2 4-methyl-benzylpropiolate (139mg, 0.8mmol) as raw material, the operation method was the same as III-1 to obtain 75mg of white solid III-2 with a yield of 39%.

[0044] 1 H NMR (DMSO) δ7.97 (dt, J=7.7, 0.9Hz, 1H), 7.70 (td, J=7.4, 6.0Hz, 2H), 7.61 (td, J=7.5, 1.1Hz, 1H), 7.43 -7.35(m, 3H), 7.25(d, J=7.8Hz, 2H), 7.15(s, 1H), 5.35-5.25(m, 2H), 4.40-4.07(m, 4H), 2.34(s, 3H ), 1.30(t, J=7.1Hz, 3H), 1.12(t, J=7.1Hz, 3H); HRMS(ESI + )m / z 502.1473[M+Na] + .

Embodiment 3

[0045] Example 3: 3,3-diethyl-1-(4-methoxybenzyl)-9b-hydroxy-5-oxo-5,9b-dihydro-3H-pyrrolo[2,1-a ] Isoindole-1,3,3-tricarboxylate (III-3)

[0046] Using II-3 4-methoxy-benzyl propiolate (152mg, 0.8mmol) as raw material, the operation method was the same as III-1 to obtain 48mg of white solid III-3 with a yield of 24%.

[0047] 1 H NMR (DMSO): δ7.94 (dd, J=7.4, 1.7Hz, 1H), 7.73-7.62 (m, 2H), 7.62-7.53 (m, 1H), 7.49-7.32 (m, 3H), 7.11 (s, 1H), 7.02-6.89(m, 2H), 5.33-5.16(m, 2H), 4.38-4.03(m, 4H), 3.76(s, 3H), 1.26(t, J=7.1Hz, 3H ), 1.08 (t, J=7.1Hz, 3H); HRMS (ESI + )m / z 518.1436[M+Na] + .

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Abstract

The invention belongs to the field of organic chemistry, and particularly relates to a pyrrolo[2,1-a]iso-indolone compound and a synthetic method thereof. According to the synthetic method, 2-(1,3-diisoindolonyl)-diethyl malonate and active electron-deficiency alkyne are used as raw materials to react under the catalysis of triethylamine to obtain the pyrrolo[2,1-a]iso-indolone compound as shown in the following formula III, and the compound has potential medical application value. The synthetic method has advantages of wide substrate application range, simplicity in operation, moderate reaction, convenience in post-treatment, simplicity and easiness in obtaining the raw materials and catalysts, and the like. (Refer to the description).

Description

(1) Technical field [0001] The invention relates to a new method for synthesizing pyrrolo[2,1-a]isoindolinone compounds, belonging to the field of organic chemistry synthesis methodology. (2) Background technology [0002] Pyrrolo[2,1-a]isoindolinone compounds are an important class of heterocyclic compounds, which widely exist in natural products and synthetic drugs with various biological activities. The isoindolinone structure in this structure has Good antihypertensive and antitumor activity. Chlorthalidone containing isoindolinone group is an antihypertensive drug that has been widely used, and this type of structure is also widely used in CDK kinase inhibitors for the treatment of tumors (Honma, T, Anyu.Co.Jp, et al. J. Med. Chem 2001, 44, 4628). Therefore, the synthesis of pyrrolo[2,1-a]isoindolinone compounds has aroused the interest of many chemical workers. However, there are few methods for synthesizing this structure using organic bases as catalysts or acceler...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 周庆发张立张北辰陆涛
Owner CHINA PHARM UNIV
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