Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Substituded acza nember 5/nember 6 ring compound and its preparation process

A technology of compounds and benzene rings, applied in the direction of organic chemistry, etc., can solve the problems of many steps, lack of product diversity, and complicated operation.

Inactive Publication Date: 2005-06-08
YANBIAN UNIV +1
View PDF0 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the first method is easy to operate, it lacks the diversity of products due to the limitation of raw materials. The second and third methods have problems such as many steps and cumbersome operation.

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
  • Substituded acza nember 5/nember 6 ring compound and its preparation process
  • Substituded acza nember 5/nember 6 ring compound and its preparation process
  • Substituded acza nember 5/nember 6 ring compound and its preparation process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In a 100 ml Erlenmeyer flask, add 50 ml of DMF, 15.2 g (110 mmol) of anhydrous K 2 CO 3 , stirred for 10 minutes, then added amine / carbamoylacetone (500mmol), stirred for 0.5 hours, added 4 milliliters (55mmol) of carbon disulfide under ice cooling and continued to stir for 1 hour, added dihalogenated hydrocarbon (55mmol), stirred for 10 hours, poured into 150 ml of water, a large amount of white solid was precipitated, suction filtered, and dried to obtain a light yellow solid product α-ammonia / carbamoyl dithioketal 2. The reaction is shown in the following formula, and the data is shown in the table below:

[0021]

[0022] R 1 =H; R, R=(CH 2 ) 2 77.2%

[0023] R 1 =H; R, R=(CH 2 ) 3 78.5%

[0024] R 1 =H; R, R=(CH 2 ) 4 76.0%

[0025] R 1 =H; R=CH 3 73.2%

[0026] R 1 =H; R=Bn 72.0%

[0027] R 1 =ClC 6 h 4 ; R, R=(CH 2 ) 2 93.0%

[0028...

Embodiment 2

[0038] In a 100 ml Erlenmeyer flask, add 50 ml of DMF, 15.2 g (110 mmol) of anhydrous K 2 CO 3 , stirred for 10 minutes, then added 6.4 milliliters (500 mmol) of ethyl acetoacetate, stirred for 0.5 hours, added 4 milliliters (55 mmol) of carbon disulfide under ice cooling and continued to stir for 1 hour, added 1,3-dibromopropane (or 1,2- Dibromoethane and 1,4-dibromobutane) (55mmol), stirred for 10 hours, poured into 150 milliliters of water, a large amount of white solid was precipitated, filtered by suction, and dried to obtain the white solid product 2-[1,3] Ethyl dithio-2-methylene-3-oxobutyrate, yield 85.0%. The reaction is shown in the following formula, and the data are shown in the table below.

[0039]

[0040] R, R=(CH 2 ) 2 93.8%

[0041] R, R=(CH 2 ) 3 95.0%

[0042] R, R=(CH 2 ) 4 91.3%

[0043] R=CH 3 87.5%

[0044] R=Bn 86.2%

[0045] According to the hydroly...

Embodiment 3

[0056] Ethyl 2-dialkylthiomethylene-3-carbonylbutanoate (5 mmol) synthesized in Example 2 and aromatic aldehyde ArCHO (6 mmol) were added to ethanol (15 mL) and stirred in an ice-water bath for 5 min. 1N NaOEt / EtOH solution (6mL, equivalent to 6mmol EtONa, prepared now) was added dropwise, and stirred at room temperature. TLC detects that the reaction causes the disappearance of the substrate (it takes about 4 h). The solvent ethanol was evaporated under reduced pressure, and the residual solid after evaporation of ethanol was quickly washed with hydrochloric acid (10 mL, 1N), filtered with suction, washed with water, and dried to obtain a yellow solid -α-cinnamoyl-α-carboxy dithioketene.

[0057] Pour dry CH into a 50-ML dry three-necked bottle 2 Cl 2 (or THF, 10mL) and compound α-cinnamoyl-α-carboxydithioketene (2.0mmol), after stirring for 15min, add SOCl 2 (285.6mg, 2.4mmol), heated to reflux in a hot water bath for 3min under electromagnetic stirring, and stopped heati...

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

A process for one-step synthesizing 3-dialkylthiomethylene azapentacycle / hexacycle-2,4-dione from alpha-acyl-alpha-amine / ammonia formacyl dithioketene, and the compound (polysubstitutent pyrrolidone or polysubstitutent hydropyridone) prepared by said process are disclosed.

Description

Technical field: [0001] The invention discloses a method for one-step synthesis of 3-dialkylthiomethylene aza five-membered / six-membered ring-2,4-dione starting from α-acyl-α-amine / carbamoyl dithioketene The synthesis method and the compound synthesized by the method belong to the technical field of organic synthesis. Background technique: [0002] Azacyclic ketones are attracting people's attention (Lockhart I.M., Webb N.E., Wright M., Winder C.V., Vamer P..J.Med.Chem., 1972, 15, 935 and references cited therein.Martinelli M., Peterson B..Tetrahedron Lett.1990, 31, 5401.Philip M., Sabol, etc.Tetrahedron, 2003, 59, 2953 and references cited therein). Such as MG-1 and pyrrolidone drugs that have a certain effect on cardiovascular diseases (For a review, see: Palfreyman, M.N.Souness, J.E.Progress in Medicinal Chemistry, 1996, 33, 1) and drugs that have been used in clinical research Piperidinone compounds (Shorvonm, Simon.TeLancet, 2001, 358, 9296, 1885 and references cited...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/04C07D409/14C07D413/04C07D413/14C07D417/04C07D417/14
Inventor 金玉子刘群尹炳柱
Owner YANBIAN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com