Synthesis method of bithiazole-4-yl disulfide derivative

A technology based on disulfides and synthesis methods, which is applied in the field of preparation of bithiazol-4-yl disulfide derivatives, can solve problems such as bad smell and instability of mercaptans, and ensure the health of operators and strong base The effect of universal applicability and high yield

Active Publication Date: 2020-06-05
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these transformations have disadvantages such as the use of thiols with bad smell or unstable disulfur dichloride, and the great limitation of reaction substrates.

Method used

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  • Synthesis method of bithiazole-4-yl disulfide derivative
  • Synthesis method of bithiazole-4-yl disulfide derivative
  • Synthesis method of bithiazole-4-yl disulfide derivative

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preparation example Construction

[0015] The invention discloses a synthesis method of bithiazol-4-yl disulfide derivatives, which comprises the following steps: using alkynyl oxime ether as a substrate, elemental sulfur as a sulfur source, and 1,8-diazabicycloundecone Carb-7-ene (DBU) as base, NMP-H 2 O(5:1,V:V) as solvent, stirred and reacted at 100℃~120℃ for 12 hours; the chemical reaction formula is as follows:

[0016]

[0017] The -R is phenyl, 4-methylphenyl, 2-methylphenyl, 4-ethylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 3 - one of chlorophenyl, 4-bromophenyl, 4-trifluoromethylphenyl, 2-naphthyl, 2-thienyl, cyclohexyl;

[0018] The -Ar is phenyl, 4-methylphenyl, 3-methylphenyl, 2-methylphenyl, 4-tert-butylphenyl, 4-methoxyphenyl, 4-fluorophenyl , 4-chlorophenyl, 4-trifluoromethylphenyl;

[0019] After the reaction was completed, after cooling, the reaction solution was filtered to obtain the filtrate, washed with saturated sodium chloride solution, extracted with ethyl acetate and...

specific Embodiment 1

[0020] Specific embodiment one: 47.0 milligrams (0.2mmol)-1,3-diphenylprop-2-yn-1-ketone o-methyl oxime, 102.4 milligrams (0.4mmol) elemental sulfur, 91.2 milligrams (0.6mmol) 1 , 8-diazabicycloundec-7-ene (DBU) was added to 2mL solvent NMP-H 2 O(5:1,V:V). The reaction was stirred at 120°C for 12 hours. Cool after the reaction, filter the reaction solution to obtain the filtrate, wash with saturated sodium chloride solution, extract with ethyl acetate and dry with anhydrous sodium sulfate, and use a rotary evaporator to remove the solvent from the filtrate to obtain a residue, which is passed through a silica gel column Use the eluent prepared by petroleum ether and ethyl acetate at a volume ratio of 30:1 for rinsing, collect the effluent according to the actual gradient, detect by TLC, combine the effluent containing the target product, and use rotary evaporation for the combined effluent Rotate the solvent to remove the solvent, and dry in vacuo to obtain 43.4 mg of yellow...

specific Embodiment 2

[0021] Specific embodiment two: 49.8 milligrams (0.2mmol) 1-phenyl-3-(p-tolyl) propyl group-2-yn-1-one oxime, 102.4 milligrams (0.4mmol) elemental sulfur, 91.2 milligrams (0.6mmol) )1,8-diazabicycloundec-7-ene (DBU) was added to 2mL solvent NMP-H 2 O(5:1,V:V). The reaction was stirred at 120°C for 12 hours. Cool after the reaction, filter the reaction solution to obtain the filtrate, wash with saturated sodium chloride solution, extract with ethyl acetate and dry with anhydrous sodium sulfate, and use a rotary evaporator to remove the solvent from the filtrate to obtain a residue, which is passed through a silica gel column Use the eluent prepared by petroleum ether and ethyl acetate at a volume ratio of 30:1 for rinsing, collect the effluent according to the actual gradient, detect by TLC, combine the effluent containing the target product, and use rotary evaporation for the combined effluent Rotate the solvent to remove the solvent, and dry in vacuo to obtain 47.4 mg of ye...

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Abstract

The invention relates to a synthetic method of a bithiazole-4-yl disulfide derivative. The synthesis method comprises the following steps: taking alkynyl oxime ether as a substrate, taking elemental sulfur as a sulfur source, taking 1,8-diazabicycloundec-7-ene as alkali and NMP-H2O (5:1, V:V) as a solvent, and carrying out a reaction at 100-120 DEG C under stirring for 12 hours. Odorless, easily available and cheap elemental sulfur is used as a sulfur source, and the method has the advantages of simple and easily available raw materials, simple operation, relatively mild conditions, wide substrate universality, high yield and good functional group compatibility.

Description

technical field [0001] The invention relates to a preparation method of bithiazol-4-yl disulfide derivatives. Background technique [0002] Disulfide bond scaffolds widely exist in natural products and drug molecules, such as drugs romidepsin, somatostatin, urofollistin, disulfiram, lanreotide, and desmopressin, etc. Therefore, how to efficiently synthesize disulfides has attracted much attention for decades. Traditionally, the oxidation of thiols is a classic way to construct symmetrical disulfide bonds (J. Am. Chem. Soc. 2002, 124, 5626). Alkyl halides and disodium disulfide (Na 2 S 2 ) or elemental sulfur cross-coupling and reduction of sulfonyl halides can also construct S-S bonds (J.Am.Chem.Soc.2018,140,30; Synth Commun.1995,25,3573; J.Chem.Res.2006 ,547). In addition, disulfur dichloride (S 2 Cl 2 ) with alkenes, heteroarenes or arylzinc halides can also be used to prepare disulfides (J.Org.Chem.1969, 34, 3991; Synlett2005, 1185); for example, Zia-ur-Rehman's gr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D275/03
CPCC07D275/03
Inventor 张小红陈倩张兴国胡伯伦
Owner WENZHOU UNIVERSITY
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