Region-selective synthesis method of 2,5-disubstituted pyrrole

A regioselective, disubstituted pyrrole technology, applied in the direction of organic chemistry, can solve the problems of substituent restrictions, limited scope of application, unstable raw materials, etc., and achieve the effect of simplifying the synthesis process and good universality

Active Publication Date: 2017-11-28
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in these synthetic methods of pyrrole, the substituents at the 2,5-position on the pyrrole are all introduced before forming the pyrrole ring, which limits the introduction of substituents.

Method used

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  • Region-selective synthesis method of 2,5-disubstituted pyrrole
  • Region-selective synthesis method of 2,5-disubstituted pyrrole

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0034] Example 1

[0035] The first step, the synthesis of compound 2

[0036]Under nitrogen protection, NaH (1.73 g, 43.2 mmol) and DMF (50 mL) were added to a 250 mL two-necked flask; pyrrole (2.42 g, 36 mmol) and DMF (20 mL) were added to a 100 mL two-necked flask, and the mixture was stirred in an ice bath. It was added dropwise to the DMF solution of NaH washed with n-hexane, stirred for 1 h; ClSO was added dropwise 2 NMe 2 (3.9 mL, 36 mmol), reacted at 0 °C for 2 h. An appropriate amount of ice water was added to the two-necked flask, extracted with ether, the organic phase was collected, washed with water and saturated brine respectively, and anhydrous Na 2 SO 4 It was dried, evaporated under reduced pressure to remove the solvent, and then separated through a column. The developing solvent was n-hexane:diethyl ether (10:1) to obtain 4.39 g of a white solid with a yield of 70.0%. mp:61-62℃; 1 H NMR (500MHz, CDCl 3 )δ2.79(s, 6H), 6.31(t, 1H, J=2 Hz), 7.09(t, 1H, ...

Example Embodiment

[0077] Example 2

[0078] The first step, the synthesis of compound 2

[0079] Under nitrogen protection, NaH (1.44g, 36mmol) and DMF (50 mL) were added to a 250mL two-necked flask; pyrrole (2.42g, 36mmol) and DMF (20mL) were added to a 100mL two-necked flask, and the mixture was stirred in an ice bath. Add dropwise to the DMF solution of NaH washed with n-hexane, stir for 1 h; add ClSO dropwise 2 NMe 2 (3.9 mL, 36 mmol), reacted at 0 °C for 2 h. An appropriate amount of ice water was added to the two-necked flask, extracted with ether, the organic phase was collected, washed with water and saturated brine respectively, and anhydrous Na 2 SO 4 It was dried, evaporated under reduced pressure to remove the solvent, and then separated through a column. The developing solvent was n-hexane:diethyl ether (10:1) to obtain 4.39 g of a white solid with a yield of 80%.

[0080] The second step, the synthesis of compound 3

[0081] Under nitrogen protection, THF (60 mL), TMP (2,2,...

Example Embodiment

[0109] Example 3

[0110] The first step, the synthesis of compound 2

[0111] Under nitrogen protection, NaH (4.32g, 108mmol) and DMF (50 mL) were added to a 250mL two-necked flask; pyrrole (2.42g, 36mmol) and DMF (20mL) were added to a 100mL two-necked flask, and the mixture was stirred in an ice bath. Add dropwise to the DMF solution of NaH washed with n-hexane, stir for 3h; add ClSO dropwise 2 NMe 2 (7.8 mL, 72 mmol), reacted at room temperature for 5 h. An appropriate amount of ice water was added to the two-necked flask, extracted with ether, the organic phase was collected, washed with water and saturated brine respectively, and anhydrous Na 2 SO 4 It was dried, evaporated under reduced pressure to remove the solvent, and then separated through a column. The developing solvent was n-hexane:diethyl ether (10:1) to obtain 4.39 g of a white solid with a yield of 70%.

[0112] The second step, the synthesis of compound 3

[0113] Under nitrogen protection, THF (60 mL...

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Abstract

The invention discloses a region-selective synthesis method of 2,5-disubstituted pyrrole and belongs to the field of chemical synthesis. According to the method, simple pyrrole is used as a starting raw material, step-by-step iodination and coupling reaction are utilized, and six-step reaction is carried out, so that a series of 2,5-disubstituted pyrrole connected with different substituent groups, yields are more than or equal to 60% respectively, and structures are confirmed by virtue of 1H NMR, 13C NMR and HRMS. Compared with the traditional Paal-Knorr synthesis method, the region-selective synthesis method disclosed by the invention has the advantages that a building block molecule does not need to be constructed in advance, cheap and easy-to-get pyrrole is used as a raw material, a synthesis process is simplified, different substituent groups can be flexibly introduced to sites 2,5 of pyrrole, and a foundation is laid for synthesizing compounds such as drugs, molecular wires and macromolecular polymers.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a regioselective synthesis method of 2,5-disubstituted pyrrole. Background technique [0002] 2,5-disubstituted pyrrole is an important class of polysubstituted pyrrole compounds, which have good biological activity or photoelectric properties, and are commonly found in natural or non-natural products with biological activity. They are many drugs, porphyrin analogs, The main structural unit of polymers, alkaloids and amino acids. 2,5-disubstituted pyrrole has a good application prospect, and its synthesis research has attracted more and more attention. [0003] At present, the synthesis methods of 2,5-disubstituted pyrrole are mainly divided into two categories, namely the ring formation of chain compounds and the functionalization of pyrrole ring. At present, there are many applications of ring-forming chain compounds, such as the traditional Paal-Knorr synthesis ...

Claims

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Application Information

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IPC IPC(8): C07D207/48
CPCC07D207/48
Inventor 刘建辉于启欣闵祥婷
Owner DALIAN UNIV OF TECH
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