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Method for synthesis of highly functionalized pyrrole compound

A synthetic method and highly functional technology, applied in organic chemistry and other directions, to achieve the effects of easy availability of raw materials and reagents, easy separation and purification, and simple operation

Inactive Publication Date: 2012-09-12
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the reaction of dialkylthio-substituted alkynes with primary amines to synthesize highly functionalized pyrroles has not been reported in the literature.

Method used

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  • Method for synthesis of highly functionalized pyrrole compound
  • Method for synthesis of highly functionalized pyrrole compound
  • Method for synthesis of highly functionalized pyrrole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 1) Dialkylthio substituted alkynes 1a preparation of

[0025]

[0026] Add acetonitrile (CH 3 CN) (4 mL), α-acetyl dithioketene (0.320g , 2.0 mmol) and 1,3-diphenylpropargyl alcohol (0.499g , 12 mmol), at room temperature 20°C, under stirring Next, TLC detects that the substrate disappears, and the reaction ends. The reaction solution was poured into saturated aqueous sodium chloride solution (10 mL), extracted with dichloromethane (3×10 mL), the organic phases were combined, dried with anhydrous calcium chloride, filtered, and then the organic solvent was distilled off under reduced pressure. Obtain solid mixture, through silica gel column chromatography (eluent is V 石油醚 : V 乙酸乙酯 = 10 : 3) 0.61g of white solid was obtained, and the structure of the product was confirmed by NMR and MS to be dialkylthio-substituted alkynes 1a , the yield is 88%.

[0027] 2) Pyrrole derivatives 2a preparation of

[0028]

[0029] To a 25 mL round bottom flask equipped with a...

Embodiment 2

[0033] use 1b Instead of the example 1 1a , the temperature is 80°C, other conditions are the same as Example 1, and the experimental results are shown in Table 1.

[0034]

[0035] Spectral analysis data 2b :

[0036] 1 H-NMR (500 MHz, CDCl 3 ) δ 2.56 (s, 3H), 3.80 (s, 2H), 4.69 (d, J = 4.5 Hz, 2H), 4.85 (s, 2H), 6.85 (d, J = 7.5 Hz, 2H), 6.91-6.99 (m, 6H), 7.153-7.30 (m, 12H); 13 C-NMR (CDCl 3 , 125 MHz) δ 11.99, 30.38, 47.36, 50.50, 111.96, 122.92, 125.58, 126.14, 126.38, 127.38, 127.45, 127.64, 127.67, 127.90, 128.29, 128.57, 128.62, 128.85, 129.22, 133.81, 136.02, 136.24, 136.67 , 138.67, 192.56; HRMS (ESI) m / z calculated for C 31 h 29 N 2 S 2 [M+1] + : 493.1772 found: 493.1672.

Embodiment 3

[0038] use 1c Instead of the example 1 1a , the temperature is 120°C, other conditions are the same as Example 1, and the experimental results are shown in Table 1.

[0039]

[0040] Spectral analysis data 2c :

[0041] 1 H-NMR (500 MHz, CDCl 3 ) δ 2.73 (s, 3H), 3.90 (s, 2H), 4.77 (d, J = 4.5 Hz, 2H), 5.00 (s, 2H), 6.88 (d, J = 7.0 Hz, 2H), 7.01-7.05 (m, 7H), 7.31 (d, J = 7.5 Hz, 2H), 7.42-7.47 (m, 8H); 13 C-NMR (CDCl 3 , 125 MHz) δ 11.84, 29.49, 47.28, 50.43, 115.27, 115.44, 120.41, 122.67, 125.56, 126.88, 127.04, 127.41, 127.65, 128.11, 128.63, 128.88, 128.91, 129.17, 129.23, 129.95, 133.56, 134.69, 134.71 , 134.90, 136.16, 136.87, 160.48, 162.43, 193.16; HRMS (ESI) m / z calculated for C 33 h 30 FN 2 S [M+1] + : 505.2114 found: 505.2079.

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Abstract

The invention belongs to the technical field of organic synthetic chemistry and especially relates to a method for synthesis of a highly functionalized pyrrole compound. The highly functionalized pyrrole compound is obtained by two reaction processes. The method for synthesis of the highly functionalized pyrrole compound comprises that functionalized ketene dithioacetal and alkynol as raw materials are synthesized into a dialkylthio-substituted enyne compound and the dialkylthio-substituted enyne compound and primary amine are prepared into the highly functionalized pyrrole compound. The method for synthesis of the highly functionalized pyrrole compound has simple processes, adopts easily available raw materials and reagents, realizes simultaneous introduction of multiple substituent groups and easy separation purification of products, and is suitable for synthesis of various highly-functionalized pyrrole compounds.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and specifically relates to a highly functionalized pyrrole compound and a synthesis method thereof. Background technique [0002] Pyrrole is an important class of heterocyclic compounds. It is not only the key structural unit of many biologically active natural products, drugs, and organic conductive materials, but also a multi-purpose organic synthon. Therefore, the development of synthetic methods for pyrrole rings has always been an important aspect of organic synthetic chemistry. One of the important research topics of ( Comprehensive Heterocyclic Chemistry III 2008, 3 , pp 45-268.; Nat. Prod. Rep. , 2006, 23 , 517-531.; ARKIVOC 2007, 10 , 121-141.). The methods that have been developed so far include: Knorr synthesis, Hantzsch reaction, Paal-Knorr condensation reaction, reductive coupling reaction, aza-Wittig reaction, multi-component coupling methodology and oth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/34C07D409/04C07D405/14
Inventor 毕锡和房忠雪宋金娜
Owner NORTHEAST NORMAL UNIVERSITY
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