Unlock instant, AI-driven research and patent intelligence for your innovation.

Sulfonyl lactone compound containing pyridine ring and preparation method thereof

A technology of sulfonyl lactone and pyridine ring, which is applied in the field of sulfonyl lactone compound containing pyridine ring and its preparation, can solve the problems of low reactivity and the like, and achieves low requirements for instruments and equipment, simple and easy-to-obtain raw materials, and high yield Effect

Inactive Publication Date: 2018-10-16
WUHAN UNIV OF TECH
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because of the electron deficiency and strong Lewis basicity of the pyridine ring, it has low reactivity, which makes the synthesis of pyridine ring-containing compounds more challenging (Heterocyclic Chemistry, 4thed)

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Sulfonyl lactone compound containing pyridine ring and preparation method thereof
  • Sulfonyl lactone compound containing pyridine ring and preparation method thereof
  • Sulfonyl lactone compound containing pyridine ring and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037]

[0038] In a 250mL reaction flask, add 2-phenyl-vinyl-sulfonyl fluoride (3.72g, 20mmol), 2-acetylpyridine (4.85g, 40mmol), Ni(NO 3 ) 2 .6H 2 O (1.16g, 4.0mmol, 20mol%), K 2 CO 3 (5.53g, 40mmol), MeCN (100mL), reacted at room temperature for 24h, and the reaction solution was extracted and purified by silica gel column chromatography (eluent was petroleum ether: ethyl acetate=5:1 (v / v)), namely 4-Phenyl-6-(pyridin-2-yl)-3,4-dihydro-1,2-oxathione 2,2-dioxide (6.70 g, 90% yield) was obtained. Mp 112-114°C. 1 H NMR (500MHz, CDCl 3 )δ8.57(d, J=4.1Hz, 1H), 7.77(td, J=7.8Hz, J=1.6Hz, 1H), 7.68(d, J=8.0Hz, 1H), 7.40(t, J= 7.1Hz, 2H), 7.36-7.32(m, 3H), 7.29(dd, J=6.7Hz, J=5.1Hz, 1H), 6.71(d, J=1.5Hz, 1H), 4.39(ddd, J= 12.1Hz, J=6.3Hz, J=2.3Hz, 1H), 3.69(dd, J=13.9Hz, J=6.2Hz, 1H), 3.37(dd, J=13.6Hz, J=12.5Hz, 1H). 13 C NMR (126MHz, CDCl 3 )δ149.6,149.4,149.2,139.1,137.1,129.4,128.3,127.7,124.1,119.0,108.1,50.8,41.2.ESI-MS HRMS calculated for C 15 h 13 NO 3 S[M+1]...

Embodiment 2

[0040]

[0041] In a 250mL reaction flask, add 2-thienyl-vinylsulfonyl fluoride (3.84g, 20mmol), 2-acetylpyridine (4.85g, 40mmol), Ni(NO 3 ) 2 .6H 2O (1.16g, 4.0mmol, 20mol%), K 2 CO 3 (5.53g, 40mmol), MeCN (100mL), reacted at room temperature for 24h, and the reaction solution was extracted and purified by silica gel column chromatography (eluent was petroleum ether: ethyl acetate=5:1 (v / v)), namely 6-(pyridin-2-yl)-4-(thiophen-3-yl)-3,4-dihydro-1,2-oxathione 2,2-dioxide (6.45g, 84 %yield). Mp 87-89°C. 1 H NMR (500MHz, CDCl 3 )δ8.57(d, J=3.4Hz, 1H), 7.77(t, J=8.7Hz, 1H), 7.66(d, J=7.7Hz, 1H), 7.38(s, 1H), 7.30-7.26( m,1H),7.24(s,1H),7.06(d,J=4.6Hz,1H),6.72(s,1H),4.54-4.51(m,1H),3.72(dd,J=14.1Hz,J =6.6Hz, 1H), 3.39(t, J=12.5Hz, 1H),. 13 C NMR (126MHz, CDCl 3 )δ149.6, 149.2, 148.8, 139.2, 137.1, 127.4, 126.4, 124.1, 122.5, 119.0, 107.7, 50.1, 36.4. ESI-MS HRMS calculated for C 13 h 11 NO 3 S 2 [M+1] + 341.0954found 341.0954.

Embodiment 3

[0043]

[0044] In a 250mL reaction flask, add 2-phenyl-vinyl-sulfonyl fluoride (3.72g, 20mmol), 6,7-dihydroquinolin-8(5H)-one (5.89g, 40mmol), Ni(NO 3 ) 2 .6H 2 O (1.16g, 4.0mmol, 20mol%), K 2 CO 3 (5.53g, 40mmol), MeCN (100mL), reacted at room temperature for 24h, and the reaction solution was extracted and purified by silica gel column chromatography (eluent was petroleum ether: ethyl acetate=5:1 (v / v)), namely 4-Phenyl-3,4,5,6-tetrahydro-[1,2]oxathiano[5,6-h]quinoline 2,2-dioxide (7.37g, 99% yield). Mp 178-180°C. 1 H NMR (500MHz, CDCl 3 )δ8.53(d,J=2.8Hz,1H),7.43-7.35(m,4H),7.28(d,J=7.2Hz,2H),7.17-7.15(m,1H),4.28-4.25(m ,1H),3.69(dd,J=13.9Hz,J=6.6Hz,1H),3.36(t,J=12.3Hz,1H),2.90-2.83(m,1H),2.78-2.72(m,1H) ,2.17-2.13(m,2H). 13 C NMR (126MHz, CDCl 3 )δ147.8, 147.0, 144.5, 138.0, 134.9, 131.3, 129.5, 128.5, 128.3, 123.4, 120.5, 51.6, 46.1, 26.3, 25.0. ESI-MS HRMS calculated for C 17 h 15 NO 3 S[M+1] + 341.0954,found 341.0954.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a sulfonyl lactone compound containing pyridine ring and a preparation method thereof. 2-aryl vinylsulfonyl fluoride is used as a raw material, and is mixed with 2-acetyl azarene or 6,7-dihydro-5H-quinolin-8-one, additive, nickel catalyst and solvent, the mixture reacts for 24 hours or more at room temperature, then the product is separated and purified so as to obtain thefinal product sulfonyl lactone compound containing pyridine ring. Innovatively, the preparation method has the advantages that the reaction condition is mild, the requirement on the instrument equipment is low, the operation is simple and yield is high, the raw materials are easy to obtain, and method is suitable for mass production in laboratory or industrial production amplification. The productsulfonyl lactone compound containing pyridine ring has a potential pharmaceutical prospect after being researched and optimized subsequently.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a sulphonyl lactone compound containing a pyridine ring and a preparation method thereof. Background technique [0002] Pyridines are a class of six-membered nitrogen-containing electron-deficient heteroaromatics. Substituted pyridines have a wide range of biological activities and are listed as the most common heterocyclic compounds in medicinal chemistry and pharmaceutical industry (Chem. Rev., 2005, 105, 5592). There are more than one hundred drugs containing at least one pyridine ring approved by the U.S. Food and Drug Administration, including esomeprazole (Nexium), loratadine (Claritin) and imatinib (Gleevec). Drugs (Chem. 2013, 5, 54). Due to the importance of the pyridine moiety, it is of great significance to construct a method with mild reaction conditions to synthesize compounds containing pyridine rings. Because of the electron deficiency and strong Lewi...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D411/04C07D411/14C07D497/04
CPCC07D411/04C07D411/14C07D497/04
Inventor 秦华利蒋莹陈兴
Owner WUHAN UNIV OF TECH