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1-Acetyl-2-imidazolidinone, also known as Clonidine EP Impurity A, is a synthetic reagent with a chemical structure that plays a significant role in the pharmaceutical industry. It is characterized by its unique properties that make it suitable for various applications, particularly in the synthesis of specific compounds.

5391-39-9

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5391-39-9 Usage

Uses

Used in Pharmaceutical Industry:
1-Acetyl-2-imidazolidinone is used as a synthetic reagent for the preparation of triple [14C]-labelled moxonidine, an antihypertensive compound. Its role in the synthesis process is crucial for the development of this medication, which is designed to help regulate blood pressure and manage hypertension-related conditions. The use of 1-Acetyl-2-imidazolidinone in this context highlights its importance in the pharmaceutical sector, contributing to the development of life-saving drugs.

Check Digit Verification of cas no

The CAS Registry Mumber 5391-39-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,3,9 and 1 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 5391-39:
(6*5)+(5*3)+(4*9)+(3*1)+(2*3)+(1*9)=99
99 % 10 = 9
So 5391-39-9 is a valid CAS Registry Number.
InChI:InChI=1/C5H8N2O2/c1-4(8)7-3-2-6-5(7)9/h2-3H2,1H3,(H,6,9)

5391-39-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Acetyl-2-imidazolidinone

1.2 Other means of identification

Product number -
Other names 1-acetylimidazolidin-2-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5391-39-9 SDS

5391-39-9Synthetic route

imidazolidone
120-93-4

imidazolidone

acetic anhydride
108-24-7

acetic anhydride

1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

Conditions
ConditionsYield
With water for 0.5h; Heating;88%
at 150℃; for 1h;64.1%
for 0.5h; Reflux;63%
imidazolidone
120-93-4

imidazolidone

1-acetyl-1H-benzotriazole
18773-93-8

1-acetyl-1H-benzotriazole

1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

Conditions
ConditionsYield
Stage #1: imidazolidone With potassium carbonate In toluene at 20℃; for 0.5h;
Stage #2: 1-acetyl-1H-benzotriazole In toluene at 80℃; for 2h;
87%
imidazolidone
120-93-4

imidazolidone

Benzyl isocyanide
88333-03-3, 10340-91-7

Benzyl isocyanide

acetyl chloride
75-36-5

acetyl chloride

A

1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

B

1-(benzyliminomethyl)imidazolin-2-one hydrochloride

1-(benzyliminomethyl)imidazolin-2-one hydrochloride

Conditions
ConditionsYield
In acetonitrile at 20℃; for 9h;A n/a
B 77%
imidazol-2-one
65118-65-2

imidazol-2-one

acetyl chloride
75-36-5

acetyl chloride

1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

Conditions
ConditionsYield
In tetrahydrofuran52%
In tetrahydrofuran52%
In tetrahydrofuran52%
In tetrahydrofuran52%
monoacetylaminoethylamine
1001-53-2

monoacetylaminoethylamine

carbon dioxide
124-38-9

carbon dioxide

1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

Conditions
ConditionsYield
With cerium(IV) oxide In ethanol at 160℃; for 8h;9%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

Vinyl bromide
593-60-2

Vinyl bromide

1-acetyl-3-vinyl-2-imidazolidone

1-acetyl-3-vinyl-2-imidazolidone

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In tetrahydrofuran at 80℃; for 9h; Inert atmosphere; Schlenk technique;94.4%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine
41730-71-6

1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine

Conditions
ConditionsYield
In benzene at 55 - 60℃; for 3h; chloroformylation;93.8%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

5-chloro-N-(1-acetyl-4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazole-4-amine

5-chloro-N-(1-acetyl-4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazole-4-amine

Conditions
ConditionsYield
With trichlorophosphate In acetone at 50 - 55℃; for 20h; Temperature; Solvent;93.6%
With thionyl chloride In toluene at 65℃; Reagent/catalyst; Solvent;67%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine
41730-71-6

1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine

Conditions
ConditionsYield
With pyridine In benzene at 50 - 55℃; for 2h; Addition;92%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

tizanidine hydrochloride
64461-82-1, 74113-36-3

tizanidine hydrochloride

Conditions
ConditionsYield
Stage #1: 1-acetylimidazolidin-2-one; 4-amino-5-chloro-2,1,3-benzothiadiazole With trichlorophosphate at 60 - 65℃; for 36h;
Stage #2: With methanol for 4h; Reflux;
Stage #3: With hydrogenchloride In ethanol at 20℃; for 1h;
85%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

5-bromo-2-methyl-1H-indole
1075-34-9

5-bromo-2-methyl-1H-indole

5-Bromo-3-(4,5-dihydroimidazol-2-yl)-2-methyl-1H-indole
227801-59-4

5-Bromo-3-(4,5-dihydroimidazol-2-yl)-2-methyl-1H-indole

Conditions
ConditionsYield
Stage #1: 1-acetylimidazolidin-2-one; 5-bromo-2-methyl-1H-indole With trichlorophosphate at 50℃;
Stage #2: With ethanol Heating;
80%
Stage #1: 1-acetylimidazolidin-2-one; 5-bromo-2-methyl-1H-indole With trichlorophosphate at 50℃;
Stage #2: With ethanol Heating / reflux;
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

5-bromo-2-methyl-1H-indole
1075-34-9

5-bromo-2-methyl-1H-indole

5-bromo-3-(4,5-dihydro-1H-imidazol-2-yl)-2-methyl-1H-indole hydrochloride

5-bromo-3-(4,5-dihydro-1H-imidazol-2-yl)-2-methyl-1H-indole hydrochloride

Conditions
ConditionsYield
80%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

C5H6Cl4N2OP(1+)*Cl6P(1-)

C5H6Cl4N2OP(1+)*Cl6P(1-)

Conditions
ConditionsYield
With phosphorus pentachloride In chloroform at 20℃; for 24h;79%
2-chloro-3-aminopyridine
6298-19-7

2-chloro-3-aminopyridine

1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

1-acetyl-2-[3-(2-chloropyridinyl)]iminoimidazolidine

1-acetyl-2-[3-(2-chloropyridinyl)]iminoimidazolidine

Conditions
ConditionsYield
With trichlorophosphate for 3h; Condensation; Heating;74%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

4-aminoindan
32202-61-2

4-aminoindan

N-(1-Acetyl-2-imidazolin-2-yl)-N-(4-indanyl)amin
67356-94-9

N-(1-Acetyl-2-imidazolin-2-yl)-N-(4-indanyl)amin

Conditions
ConditionsYield
With trichlorophosphate at 50℃; for 40h;73.1%
5-chloro-2-(2-tolyl)indole

5-chloro-2-(2-tolyl)indole

1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

5-chloro-3-(4,5-dihydro-1H-imidazol-2-yl)-2-(2-methylphenyl)-1H-indole

5-chloro-3-(4,5-dihydro-1H-imidazol-2-yl)-2-(2-methylphenyl)-1H-indole

Conditions
ConditionsYield
73%
15.8%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

sodium sulfate anhydride

sodium sulfate anhydride

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

tizanidine
51322-75-9

tizanidine

Conditions
ConditionsYield
With trichlorophosphate In methanol; sodium hydroxide; water73%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

2-(4-methylphenyl)-5-trifluoromethoxy-1H-indole
227803-32-9

2-(4-methylphenyl)-5-trifluoromethoxy-1H-indole

3-(4,5-dihydroimidazol-2-yl)-2-(4-methylphenyl)-5-trifluoromethoxy-1H-indole hydrochloride

3-(4,5-dihydroimidazol-2-yl)-2-(4-methylphenyl)-5-trifluoromethoxy-1H-indole hydrochloride

Conditions
ConditionsYield
Stage #1: 1-acetylimidazolidin-2-one; 2-(4-methylphenyl)-5-trifluoromethoxy-1H-indole With trichlorophosphate at 60℃; for 20h;
Stage #2: In ethanol at 60℃; for 5h;
70%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

tizanidine
51322-75-9

tizanidine

Conditions
ConditionsYield
Stage #1: 1-acetylimidazolidin-2-one; 4-amino-5-chloro-2,1,3-benzothiadiazole With trichlorophosphate at 60 - 65℃; for 36h;
Stage #2: With methanol; sodium hydroxide for 4h; Reflux;
70%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

2,6-diethylaniline
579-66-8

2,6-diethylaniline

1-acetyl-N-(2,6-diethylphenyl)-4,5-dihydro-1H-imidazol-2(3H)-imine
86861-31-6

1-acetyl-N-(2,6-diethylphenyl)-4,5-dihydro-1H-imidazol-2(3H)-imine

Conditions
ConditionsYield
With trichlorophosphate for 3h; Heating;69.9%
5-chloro-2-m-tolyl-1H-indole

5-chloro-2-m-tolyl-1H-indole

1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

3-(4,5-dihydro-1H-imidazol-2-yl)-5-chloro-2-(3-methylphenyl)-1H-indole hydrochloride

3-(4,5-dihydro-1H-imidazol-2-yl)-5-chloro-2-(3-methylphenyl)-1H-indole hydrochloride

Conditions
ConditionsYield
68%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

2-(4-methylphenyl)-5-chloro-1H-indole
66866-07-7

2-(4-methylphenyl)-5-chloro-1H-indole

5-Chloro-3-(4,5-dihydroimidazol-2-yl)-2-(4-methylphenyl)-1H-indole

5-Chloro-3-(4,5-dihydroimidazol-2-yl)-2-(4-methylphenyl)-1H-indole

Conditions
ConditionsYield
Stage #1: 1-acetylimidazolidin-2-one; 2-(4-methylphenyl)-5-chloro-1H-indole With trichlorophosphate at 50℃;
Stage #2: With ethanol Heating;
67%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

2-ethyl-5-chloro-1H-indole
366448-75-1

2-ethyl-5-chloro-1H-indole

5-chloro-3-(4,5-dihydro-1-H-imidazol-2-yl)-2-ethyl-1H-indole

5-chloro-3-(4,5-dihydro-1-H-imidazol-2-yl)-2-ethyl-1H-indole

Conditions
ConditionsYield
Stage #1: 1-acetylimidazolidin-2-one; 2-ethyl-5-chloro-1H-indole With trichlorophosphate at 50℃;
Stage #2: With ethanol Heating;
67%
7.1%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

4-(4-(chloromethyl)phenyl)-2-(2,6-difluorophenyl)-4,5-dihydrooxazole

4-(4-(chloromethyl)phenyl)-2-(2,6-difluorophenyl)-4,5-dihydrooxazole

1-acetyl-3-(4-(2-(2,6-difluorophenyl)-4,5-dihydrooxazol-4-yl)benzyl)imidazolidin-2-one

1-acetyl-3-(4-(2-(2,6-difluorophenyl)-4,5-dihydrooxazol-4-yl)benzyl)imidazolidin-2-one

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide In toluene at 20℃; for 5h;67%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

4-chloro-2-methyl-1H-indole
6127-16-8

4-chloro-2-methyl-1H-indole

4-chloro-3-(4,5-dihydro-1H-imidazol-2-yl)-2-methyl-1H-indole hydrochloride

4-chloro-3-(4,5-dihydro-1H-imidazol-2-yl)-2-methyl-1H-indole hydrochloride

Conditions
ConditionsYield
66%
C14H9Cl2N

C14H9Cl2N

1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

3-(4,5-dihydro-1H-imidazol-2-yl)-5-chloro-2-(2-chlorophenyl)-1H-indole hydrochloride

3-(4,5-dihydro-1H-imidazol-2-yl)-5-chloro-2-(2-chlorophenyl)-1H-indole hydrochloride

Conditions
ConditionsYield
66%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

3-amino-2-methylchromone hydrochloride

3-amino-2-methylchromone hydrochloride

1-acetyl-2-(2-methyl-4-oxo-4H-benzopyran-3-yl)iminoimidazolidine

1-acetyl-2-(2-methyl-4-oxo-4H-benzopyran-3-yl)iminoimidazolidine

Conditions
ConditionsYield
With trichlorophosphate Condensation;65%
C15H11Cl2N

C15H11Cl2N

1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

3-(4,5-dihydro-1H-imidazol-2-yl)-5-chloro-2-(3-methyl-4-chlorophenyl)-1H-indole hydrochloride

3-(4,5-dihydro-1H-imidazol-2-yl)-5-chloro-2-(3-methyl-4-chlorophenyl)-1H-indole hydrochloride

Conditions
ConditionsYield
65%
2-(4-methoxyphenyl)-5-chloro-1H-indole

2-(4-methoxyphenyl)-5-chloro-1H-indole

1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

5-chloro-3-(4,5-dihydro-1H-imidazol-2-yl)-2-(4-methoxyphenyl)-1H-indole hydrochloride

5-chloro-3-(4,5-dihydro-1H-imidazol-2-yl)-2-(4-methoxyphenyl)-1H-indole hydrochloride

Conditions
ConditionsYield
64.8%
45%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

5-methoxy-2-methyl-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole

5-methoxy-2-methyl-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole

Conditions
ConditionsYield
Stage #1: 1-acetylimidazolidin-2-one; 5-methoxy-2-methyl-1H-indole With trichlorophosphate at 50℃;
Stage #2: With ethanol Heating;
64%
14.6%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

diisopropyl hydrogenphosphonate
1809-20-7

diisopropyl hydrogenphosphonate

diisopropyl(3-acetyl-2-oxoimidazolidin-1-yl)phosphonate
1417780-53-0

diisopropyl(3-acetyl-2-oxoimidazolidin-1-yl)phosphonate

Conditions
ConditionsYield
With 6,6'-dimethyl-2,2'-bipyridine; copper diacetate In toluene at 80℃; under 760.051 Torr; for 1.5h; Reagent/catalyst; Molecular sieve;64%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

2-phenyl-indole
948-65-2

2-phenyl-indole

2-phenyl-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole hydrochloride

2-phenyl-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole hydrochloride

Conditions
ConditionsYield
63.9%

5391-39-9Relevant academic research and scientific papers

N-VINYLIMIDAZOLIDONE COMPOUND, AND POLYMER THEREOF

-

Paragraph 0087-0089, (2017/01/02)

PROBLEM TO BE SOLVED: To provide an N-vinylimidazolidone compound polymer that is expected to be applied for a cell culture material, a temperature-responsive material and others. SOLUTION: The present invention provides a polymer polymerized with an N-vinylimidazolidone compound (1) as a monomer, or a copolymer comprising the monomer and a monomer of a different structure (R1 is H, C1-12 alkyl or acyl; R2 and R3 is H or methyl). SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

C-N Bond forming reactions in the synthesis of substituted 2-aminoimidazole derivatives

Gomez-SanJuan, Asier,Botija, Jose Manuel,Mendez, Almudena,Sotomayor, Nuria,Letea, Esther

, p. 44 - 56 (2014/03/21)

Carbon-nitrogen bond forming reactions oriented to the synthesis of 2-amino-imidazolidines and imidazoles have been investigated. The C-2 amination of imidazolidinones, via the corresponding 2-chlorodihydroimidazoles, led to 2-benzylaminodihydroimidazole or bis(dihydroimidazole)amino derivatives by choosing the adequate experimental conditions. On the other hand, the use of N-acyl-2-methylsulfanyldihydroimidazoles allowed carrying out the reactions with aromatic amines, such as p-anisidine. Finally, palladium catalyzed Buchwald- Hartwig amination was the method of choice for C-N coupling between 2-haloimidazoles and aromatic amines in the synthesis of the corresponding imidazoles.

CO2-Fixation on Aliphatic α,ω-Diamines to Form Cyclic Ureas, Catalyzed by Ceria Nanoparticles that were Obtained by Templating with Alginate

Primo, Ana,Aguado, Eric,Garcia, Hermenegildo

, p. 1020 - 1023 (2013/05/08)

Ceria nanoparticles (average particle size: 8nm) have been obtained by the calcination of alginate aerogel beads that were precipitated from aqueous solutions of (NH4)2Ce(NO3)6. These nanoparticles were considerably more active as a catalyst for CO2-insertion into aliphatic α,ω-diamines than the analogous commercial CeO2 with larger particle size (40nm). CeO2 that was obtained by templating with the natural alginate biopolymer afforded the cyclic urea of ethylenediamine in EtOH solvent at 160°C in 37% yield. This yield is remarkable for a process that involves CO2 as a feedstock. Other α,ω-diamines, such as diethylenetriamine, N,N′-dimethylethylenediamine, N-(2-aminoethyl)acetamide, and 1,4-diaminobutane, also formed their corresponding cyclic ureas in 4-36% yield. The catalyst lost activity upon reuse, thereby leading to severe deactivation that was only partially recovered by washing with aqueous acidic solutions.

A novel and efficient reaction of imidazolidin-2-one and N-acylbenzotriazoles: A facile synthesis of 1-acylimidazolidin-2-one

Li, Jianjun,Sun, Yan,Chen, Zhiwei,Su, Weike

experimental part, p. 3669 - 3677 (2011/02/23)

Acylation of imidazolidin-2-one with readily available N- acylbenzotriazoles, in the presence of K2CO3, produced 1-acylimidazolidin-2-ones and N,N'-diacyl-imidazolidin-2-one in moderate to good yields. The utilization of N-acylbenzotriazoles which make the reaction simple and mild, may be especially advantageous when the corresponding acid chlorides are not stable or not easily prepared. It's also an example of the reaction of N-acylbenzotriazoles and amide. Copyright

First practical synthesis of formamidine ureas and derivatives

Ripka, Amy S.,Diaz, David D.,Sharpless, K. Barry,Finn

, p. 1531 - 1533 (2007/10/03)

(Matrix presented) Isonitriles and ureas undergo a condensation reaction in the presence of acid chlorides to give formamidine ureas, for which no general synthetic routes currently exist. A mechanism is proposed in which the key intermediate is an electrophilic adduct of isonitrile and acid chloride. The process is tolerant of moderate variability in the nature of the components, and access to formamidine ureas of varying substitution patterns is further enhanced by a facile exchange reaction with amines.

Enantioselective Norrish-Yang cyclization reactions of N-(ω-oxo-ω-phenylalkyl)-substituted imidazolidinones in solution and in the solid state

Bach, Thorsten,Aechtner, Tobias,Neumueller, Bernhard

, p. 2464 - 2475 (2007/10/03)

The four N-(ω-oxo-ω-phenyl-alkyl)-substituted imidazolidinones 5-8 were prepared from N-acetylimidazolidinone (4). Upon irradiation, these substrates underwent Norrish-Yang cyclization to the racemic products rac-9-rac-12 (51-75%). The reactions of the N-2-oxoethylimidazolidinones 5 and 6 were conducted in tBuOH, and yielded 1:1 mixtures of exolendo diastereoisomers rac-9a/rac-9b and rac-10a/rac-10b, accompanied by Norrish type II cleavage products. The reactions of the N-3-oxopropylimidazolidinones 7 and 8 were performed in toluene. The exo diastereoisomers rac-11a and rac-12a were the major diastereoisomers (d.r. ? 4:1). In the presence of the chiral compounds 1-3, the photocyclization of substrate 8 proceeded with significant enantiomeric excess (5-60% ee). The more sophisticated complexing agents 3 and ent-3 provided better enantiofacial differentiation (up to 60 % ee) than the lactams 1 and 2 (up to 26 % ee). Low temperatures and an excess of the complexing agent helped to increase the enantioselectivity. The absolute configuration of the major exo product 12a obtained from compound 8 in the presence of complexing agent 3 was unambiguously established by single-crystal X-ray crystallography of its chiral N-methoxyphenylacetyl derivative 15a. In a similar fashion, the absolute configurations of the endo products 12b and ent-12b were established. The N-2-oxoethylimidazolidinone 5, which crystallized in a chiral space group, was irradiated in the solid state. At low levels of conversion, the product 9a/ent-9a was formed with high enantiomeric excess (78% ee). The enantioselectivity deteriorated at higher levels of conversion.

Penicillins

-

, (2008/06/13)

Penicillins of the formula EQU1 or pharmaceutically acceptable non-toxic salts thereof, wherein C is a carbon atom constituting a center of chirality; A is a moiety of the formula EQU2 or EQU3 wherein X is EQU4 Y is EQU5 or wherein Aryl is an aryl moiety; Z is EQU6 Q1 is EQU7 or SPC1 Q2 is EQU8 SPC2 or SPC3 R is straight-chain or branched alkyl of 1 to 5 carbon atoms; R1 is alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkenyl of 3 to 10 carbon atoms, vinyl, arylvinyl, mono-, di-, or tri-halo-lower alkyl, H2 N--, R--NH--, (R)2 N--, aryl--NH--, aryl-lower alkylamino, alkoxy of 1 to 8 carbon atoms, aralkoxy of 1 to 8 carbon atoms in the alkoxy portion, cycloalkoxy of 3 to 7 carbon atoms, aryloxy, R--O--V--, R--S-- V--, N=C--V--, R--O--CO--V--, H2 N--CO--V--, R--NH--CO--V--, R--O--CO--NH--, R--SO2 --NH--, (R)2 N--CO--V--, wherein R is as above defined, SPC4 SPC5 provided that when X is --SO2 --, R1 is not alkoxy, aralkoxy, cycloalkoxy or aryloxy, and further provided that R1 can also be hydrogen when X is --CO--; V is a divalent organic radical of 1 to 3 carbon atoms; n is 0, 1 or 2; R2 and R3 are the same or different and are each hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, vinyl, allyl, propenyl, cycloalkyl of 3 to 6 carbon atoms, cycloalkenyl of 3 to 6 carbon atoms, mono-, di- or tri-halo lower alkyl or aryl; R4, r5 and R6 are the same or different and are each hydrogen, nitro, cyano, (R)2 N--, (R)2 N--CO--, R--CO--NH--, R--O--CO--, R--CO--O--, R--, R--O--, wherein R is as above defined, H2 N--SO2 --, chlorine, bromine, iodine, fluorine or trifluoromethyl; G is hydrogen or straight or branched chain alkyl of 1 to 5 carbon atoms; and B is a moiety of the formula SPC6 wherein R7, r8 ad R9 are the same or different and are each hydrogen, halogen, nitro, hydroxy, R--, R--0--, R--S--, R--SO--, R--SO2 --, (R)2 N--, R--CO--NH--, or R--CO--O--, wherein R is as above defined; the arrow in the divalent linking group → means that the linkage of two atoms by the free valencies of his group must take place as indicated by the arrow; exhibit activity against both Gram-positive and Gram-negative bacteria.

Penicillins

-

, (2008/06/13)

Penicillins of the formula EQU1 or pharmaceutically acceptable non-toxic salts thereof, wherein C* is a carbon atom constituting a center of chirality; A is a moiety of the formula EQU2 or EQU3 wherein X is EQU4 Y is EQU5 or wherein Aryl is an aryl moiety; Z is EQU6 Q1 is EQU7 or SPC1 Q2 is EQU8 SPC2 or SPC3 R is straight- chain or branched alkyl of 1 to 5 carbon atoms; R1 is alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkenyl of 3 to 10 carbon atoms. vinyl, arylvinyl, mono-, di-, or tri-halo-lower alkyl, H2 N--, R--NH--, (R)2 N--, aryl--NH--, aryl-lower alkylamino, alkoxy of 1 to 8 carbon atoms, aralkoxy of 1 to 8 carbon atoms in the alkoxy portion, cycloalkoxy of 3 to 7 carbon atoms, aryloxy, R--O--V--, R--S--V--, N=C--V--, R--O--CO--V--, H2 N--CO--V--, R--NH--CO--V--, R--O--CO--NH--, R--SO2 --NH--, (R)2 N--CO--V--, wherein R is as above defined, SPC4 SPC5 provided that when X is --SO2 --, R1 is not alkoxy, aralkoxy, cycloalkoxy or aryloxy, and further provided that R1 can also be hydrogen when X is --CO--; V is a divalent organic radical of 1 to 3 carbon atoms; n is 0, 1 or 2; R2 and R3 are the same or different and are each hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, vinyl, allyl, propenyl, cycloalkyl of 3 to 6 carbon atoms, cycloalkenyl of 3 to 6 carbon atoms, mono-, di- or tri-halo lower alkyl or aryl; R4, r5 and R6 are the same or different and are each hydrogen, nitro, cyano, (R)2 N--, (R)2 N--CO--, R--CO--NH--, R--O--CO--, R--CO--O--, R--, R--O--, wherein R is as above defined, H2 N--SO2 --, chlorine, bromine, iodine, fluorine or trifluoromethyl; G is hydrogen or straight or branched chain alkyl of 1 to 5 carbon atoms; and B is a moiety of the formula SPC6 wherein R7, r8 and R9 are the same or different and are each hydrogen, halogen, nitro, hydroxy, R--, R--O--, R--S--, R--SO-- , R--SO2 --, (R)2 N--, R--CO--NH--, or R--CO--O-- , wherein R is as above defined; the arrow in the divalent linking group ←Q2 → means that the linkage of two atoms by the free valencies of this group must take place as indicated by the arrow; exhibit activity against both Gram-positive and Gram-negative bacteria.

Penicillins

-

, (2008/06/13)

Arylmethyl- and cyclohexenylmethyl- penicillins, substituted on the α-carbon atom of the side chain by a 2,3-disubstituted imidazolidinylcarbamido or a 2,3-disubstituted imidazolidinylthiocarbamido group, or by the corresponding 2,3-disubstituted 1,3-diazacyclohexylcarbamido or thiocarbamido groups are anti-bacterial agents.

Penicillins

-

, (2008/06/13)

Arylmethyl- and cyclohexenylmethyl- penicillins, substituted on the αcarbon atom of the side chain by a 2,3-disubstituted imidazolidinylcarbamido or a 2,3-disubstituted imidazolidinylthiocarbamido group, or by the corresponding 2,3-disubstituted 1,3-diazacyclohexylcarbamido or thiocarbamido groups are anti-bacterial agents.

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