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Synthetic method of coumarin-pyrrole compound

A synthetic method and compound technology, applied in the field of synthesis of coumarin-pyrrole compounds, can solve the problems of low utilization rate of starting materials, limited use range, harsh reaction conditions, etc., to promote deep-level expansion and not harsh storage conditions , stable effect

Inactive Publication Date: 2013-08-07
HUBEI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these methods can effectively synthesize pyrrole derivatives, there are still many obvious defects in these classic reactions, such as low utilization rate of starting materials, many reaction steps, harsh reaction conditions, etc., which limit the scope of use of the above methods

Method used

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  • Synthetic method of coumarin-pyrrole compound
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] coumarins 1a (0.2 mmol), disubstituted acetylenes 2a (0.6 mmol), palladium acetate (0.02 mmol) and copper acetate (0.04 mmol) were added to DMSO (2 mL). The reaction mixture was stirred at normal temperature and pressure under an oxygen atmosphere for 72 hours. After the completion of the reaction monitored by TLC, the organic solvent was distilled off under reduced pressure to obtain the crude product, and the product was obtained by flash column chromatography (ethyl acetate: n-hexane = 1:4) 3aa (90%). 1 H NMR (500 MHz, d 6 -DMSO, 298 K): δ 12.80 (s, 1H), 8.37–8.17 (m, 1H), 7.56–7.20 (m, 13H). 13 C NMR (125 MHz, d 6 -DMSO, 298 K): δ 157.74, 151.61, 135.78, 133.88, 133.55, 131.49, 131.07, 129.24, 128.82, 128.18, 128.09, 127.14, 124.39, 122.11, 121.09, 117.00, 113.86, 107.29, 40.73, 40.46, 40.18, 39.90, 39.62, 39.35, 39.07. HRMS (ESI): Calculated [C 23 h 15 NO 2 +H] + 338.1176, actual value 338.1177.

Embodiment 2

[0029]

[0030] The operation steps are the same as in Example 1, and the yield is 89%. 1 H NMR (500 MHz, d 6 -DMSO, 298 K): δ 12.72 (s, 1H), 8.11 (s, 1H), 7.65–7.08 (m, 12H), 2.43 (s, 3H). 13 C NMR (125 MHz, d 6 -DMSO, 298 K): δ 157.87, 149.80, 135.82, 133.73, 133.61, 133.49, 131.48, 131.06, 130.09, 128.80, 128.70, 128.13, 128.10, 127.14, 121.91, 121.06, 116.77, 113.52, 107.32, 40.73, 40.46, 40.18, 39.90, 39.62, 39.35, 39.07, 20.99. HRMS (ESI): Calculated [C 24 h 17 NO 2 -H] - 350.1187, actual value 350.1197.

Embodiment 3

[0032]

[0033] The operation steps are the same as in Example 1, and the yield is 99%. 1 H NMR (500 MHz, d 6-DMSO, 298 K): δ 12.75 (s, 1H), 8.16 (s, 1H), 7.65–6.92 (m, 12H), 2.74 (q, J = 7.6 Hz, 2H), 1.30 (t, J = 7.6 Hz, 3H). 13 C NMR (125 MHz, d 6 -DMSO, 298 K): δ 158.01, 150.04, 139.93, 136.07, 133.85, 133.70, 131.62, 131.17, 129.18, 128.93, 128.85, 128.27, 128.22, 127.25, 121.15, 120.79, 116.91, 113.68, 107.36, 40.73, 40.46, 40.18, 39.90, 39.62, 39.35, 39.07, 28.18, 15.89. HRMS (ESI): Calculated [C 25 h 19 NO 2 -H] - 364.1343, actual value 364.1346.

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Abstract

The invention discloses a synthetic method of a coumarin-pyrrole compound. The synthetic method comprises the following step of: in a reactive solvent, with 4-amino coumarin compounds and disubstituted acetylene compounds as raw materials, under the catalysis of palladium (II) and action of an oxidant, carrying out a reaction to obtain the coumarin-pyrrole compound. The synthetic method is mild in reaction conditions, simple and convenient in route and high in atom economy and has a favorable industrial application prospect; and raw materials are low in cost and easy to obtain.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and specifically relates to a synthesis method of coumarin-pyrrole compounds. Background technique [0002] Since nitrogen heterocycles are ubiquitous in natural products and medicines, they are the key areas of research. As we all know, pyrrole is a five-membered nitrogen-containing heterocyclic compound, and many drug molecules contain such a skeleton, so it is used as a basic building block in medicinal chemistry, such as formula A, a hypolipidemic drug marketed by Pfizer under the trade name Lipitor Atorvastatin (Atorvastatin) 1. Lamellarin D (Lamellarin D), which is cytotoxic to many different cancer cells and has a strong inhibitory effect on human topoisomerase I60. 2. Non-steroidal antipyretic Anti-inflammatory drug (NSAID) Zomepirac (Zomepirac)3 and potential anticancer drug4. [0003] [0004] Formula A. Several drug molecules containing pyrrole stru...

Claims

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Application Information

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IPC IPC(8): C07D491/052
Inventor 彭艳红高涛汪舰孙绍发吴鸣虎郭海滨朱晓明黄文平
Owner HUBEI UNIV OF SCI & TECH
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