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Sulfur-containing 2, 4, 5-trisubstituted oxazole compound as well as preparation method and application thereof

A technology for compounds and oxazoles, applied in the field of organic synthesis, can solve the problems of limited scope of substrate application and high price, and achieve the effects of overcoming the complex synthesis of precursors, high synthesis yield and wide applicability

Pending Publication Date: 2022-07-26
SHANDONG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of these methods require expensive transition metal catalysts or additional oxidants, and the scope of substrate application is limited

Method used

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  • Sulfur-containing 2, 4, 5-trisubstituted oxazole compound as well as preparation method and application thereof
  • Sulfur-containing 2, 4, 5-trisubstituted oxazole compound as well as preparation method and application thereof
  • Sulfur-containing 2, 4, 5-trisubstituted oxazole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 Synthesis of Compound 1

[0043]

[0044] Step 1): add p-chlorostyrene (1.0 mmol), fluorine reagent Selectfluor (2.0 mmol) and 10 ml of methanol to a 100 ml round-bottomed flask, and stir at room temperature for 5 min. Then slowly add 10 ml of methanol solution containing 4-chlorothiophenol (1.5 mmol) dropwise, keep the temperature at 10 ~ 20 ° C and stir the reaction until the reaction is complete, after-treatment with ethyl acetate and saturated brine, The β-carbonyl sulfoxide 1' was isolated by column chromatography with a yield of 62%. Characterization of data: white solid (m.p.128-129℃); 1 HNMR(400MHz, Chloroform-d)δ 7.82(d,J=8.0Hz,2H),7.61(d,J=8.0Hz,2H),7.48(d,J=8.0Hz,2H),7.43(d,J =8.0Hz,2H),4.38(dd,J=14.4Hz,75.2Hz,2H); 13 C{ 1 H}NMR (100MHz, Chloroform-d) δ190.3, 141.6, 141.2, 138.2, 134.5, 130.4, 129.9, 129.4, 125.9, 65.8; IR (KBr): νmax 2945, 1675, 1385, 1204, 1047 (S=O), 821, 741, 495; HRMS (ESI, m / z) calcd.forC 14 H 10 Cl 2 NaO 2 S + [M...

Embodiment 2

[0047] Example 2 Synthesis of Compound 3

[0048]

[0049] Step 1): add 2-naphthalene vinylene (1.0 mmol), fluorine reagent Selectfluor (2.0 mmol) and 10 ml methanol to a 100 ml round-bottomed flask, and stir at room temperature for 5 min. Then slowly add 10 ml of methanol solution containing 4-chlorothiophenol (1.5 mmol) dropwise, keep the temperature at 10 ~ 20 ° C and stir the reaction until the reaction is complete, after-treatment with ethyl acetate and saturated brine, The corresponding β-carbonyl sulfoxide 3' was isolated by column chromatography with a yield of 81%. Characterization of data: white solid (m.p.116-117℃); 1 H NMR (400MHz, Chloroform-d) δ 8.36(s, 1H), 7.93(t, J=8.0Hz, 2H), 7.87(d, J=8.0Hz, 2H), 7.67-7.55(m, 4H), 7.47(d,J=8.0Hz,2H),4.57(dd,J=14.4Hz,104Hz,2H); 13 C{ 1 H}NMR (100MHz, Chloroform-d) δ 191.2, 141.9, 138.1, 136.2, 133.4, 132.4, 131.6, 130.0, 129.8, 129.5, 129.1, 128.1, 127.4, 126.0, 123.7, 66.2; IR (KBr): ν max 3057, 1651, 1469, 1292, 10...

Embodiment 3

[0052] Example 3 Synthesis of Compound 4

[0053]

[0054] Step 1): Add 4-methylstyrene (1.0 mmol), fluorine reagent Selectfluor (2.0 mmol) and 10 ml of methanol to a 100 ml round-bottomed flask, and stir at room temperature for 5 min. Then slowly add 10 ml of methanol solution containing 4-chlorothiophenol (1.5 mmol) dropwise, keep the temperature at 10 ~ 20 ° C and stir the reaction until the reaction is complete, after-treatment with ethyl acetate and saturated brine, The corresponding β-carbonyl sulfoxide 4' was isolated by column chromatography with a yield of 56%. Data characterization: white solid (m.p.89-90℃); 1 H NMR (400MHz, Chloroform-d) δ7.76(d, J=8.0Hz, 2H), 7.63(d, J=8.0Hz, 2H), 7.46(d, J=8.0Hz, 2H), 7.25(d , J=8.0Hz, 2H), 4.42 (dd, J=14.4 Hz, 102.8Hz, 2H); 13 C{ 1 H}NMR (100MHz, Chloroform-d) δ190.9, 145.7, 142.1, 137.9, 133.6, 129.8, 129.1, 126.0, 66.1, 22.0; IR(KBr):ν max 2948,1671,1385,1179,1047(S=O),808,498; HRMS(ESI,m / z)calcd.for C 15 H 13 ClNaO ...

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Abstract

The invention provides a sulfur-containing 2, 4, 5-trisubstituted oxazole compound which is characterized in that the sulfur-containing 2, 4, 5-trisubstituted oxazole compound has a structure as shown in a formula I, in the formula I, R1 is selected from a naphthalene ring, an aromatic heterocyclic group, C1-4 alkyl, phenyl or a benzene ring containing a substituent group on the ring; r2 is selected from cyclohexyl, benzyl, phenyl or a benzene ring containing a substituent group on the ring; and R3 is selected from C1-4 alkyl, vinyl, cyclopentyl, benzyl phenyl or a benzene ring containing a substituent group on the ring. The invention further provides a corresponding preparation method and application. The defects of complex precursor synthesis, complex reaction system, more byproducts and the like in the traditional synthesis method are overcome.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a sulfur-containing 2,4,5-trisubstituted oxazole compound and a preparation method and application thereof. Background technique [0002] Oxazole is a five-membered heterocyclic compound containing one oxygen atom and one nitrogen atom, and the oxygen atom and nitrogen atom occupy the 1 and 3 positions, respectively. Oxazole is a liquid with a smell similar to pyridine, with a boiling point of 69-70 °C, easy to be oxidized but not easy to hydrogenate, and the substituents on the ring will have a certain impact on the stability of the ring. [0003] [0004] In the 1980s, natural products with oxazole rings were isolated from marine organisms. These oxazole compounds were derived from the post-translational modification of peptides, and the research on oxazole began. Today, oxazole compounds have been widely used in the field of medicine. In the fields of nervous sys...

Claims

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Application Information

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IPC IPC(8): C07D263/46C07D263/32
CPCC07D263/46C07D263/32
Inventor 黄鑫王嘉腾
Owner SHANDONG UNIV OF TECH
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