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22047-25-2

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22047-25-2 Usage

Description

2-acetylpyrazine is white to pale yellow crystalline powder with a nutty, popcorn, bread-crust odor. It is soluble in water and stable under ordinary conditions. It is used to manufacture many polycyclic compounds and used as useful structures in pharmaceuticals and perfumes. It is a component of the folates (vitamin B compounds) and of the isoalloxazine ring nucleus of flavins. Numerous pyrazine derivatives such as pyrazine polycyclic compounds, alkyl-, alicyclic-, and alkylaryl-substituted compounds, derivatives containing oxygenated functional groups and thio-functional groups in the side-chains are used in biological, drug, flavoring and perfumery industry. 2-acetylpyrazine is used as food additive, commonly used in chocolate and baked goods.

References

[1] https://pubchem.ncbi.nlm.nih.gov/compound/Acetylpyrazine#section=Pharmacology-and-Biochemistry [2] https://en.wikipedia.org/wiki/Acetylpyrazine [3] http://www.chemicalland21.com/specialtychem/perchem/2-ACETYLPYRAZINE.htm

Chemical Properties

Different sources of media describe the Chemical Properties of 22047-25-2 differently. You can refer to the following data:
1. LIGHT YELLOW TO YELLOW-BROWNISH POWDER
2. Acetylpyrazine has a nutty, popcorn, bread crust odor. It is one of the volatile aroma components in popcorn, wheat and rye crusts.

Occurrence

Reported found in guava fruit (Psidium guajava L.), wheaten bread, other types of breads, boiled and cooked beef, grilled/roasted uncured pork, pork liver, cocoa, coffee, black tea, roasted barley, roasted filbert (Corylus avellano), roasted peanut (Arachis hypogea), roasted almond (Prunus amygdalus), scallop, filberts, popcorn and sesame oil.

Uses

Acetylpyrazine has been used in synthesis of:7-heteroaryl-pyrazolo[1,5-a]pyrimidine-3-carboxamidescopper (II) complexes with di-imine ligandsN(4) substituted thiosemicarbazones

Definition

ChEBI: 2-acetylpyrazine is a pyrazine that is substituted by an acetyl group at position 2. It has been identified as one of the volatile flavor constituents in popcorn, bread crust, vinegar, and potato snacks. It has a role as a flavouring agent. It is an aromatic ketone and a member of pyrazines.

Application

Acetylpyrazine has been widely used as an intermediate in the organic synthesis of various heterocyclic derivatives and in coupling reactions, alkylation reactions, and sensitizer ligands because of its good biological and reactive activities. For example, it is a significant reaction intermediate for producing drugs for treating malaria, epilepsy, and Parkinson's disease.

Preparation

synthesis of acetylpyrazine: By the ester condensation of EtO2 C-pyrazine; by dehydrating pyrazynamide with POCI3 and then reacting the resulting 2-cyano-pyrazine with methyl magnesium bromide.

Aroma threshold values

Detection at 62 ppb

Taste threshold values

Taste characteristics at 10 ppm: roasted, nutty, bready, yeasty with popcorn, corn chip nuance

General Description

2-Acetylpyrazine has been identified as one of the volatile flavor constituents in popcorn, wheat and rye bread crust.

Check Digit Verification of cas no

The CAS Registry Mumber 22047-25-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,0,4 and 7 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 22047-25:
(7*2)+(6*2)+(5*0)+(4*4)+(3*7)+(2*2)+(1*5)=72
72 % 10 = 2
So 22047-25-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H8N2O/c1-6(9)8-4-2-7-3-5-8/h2-5,7H,1H3

22047-25-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (A15917)  2-Acetylpyrazine, 99%   

  • 22047-25-2

  • 1g

  • 636.0CNY

  • Detail
  • Alfa Aesar

  • (A15917)  2-Acetylpyrazine, 99%   

  • 22047-25-2

  • 5g

  • 1822.0CNY

  • Detail
  • Aldrich

  • (251801)  Acetylpyrazine  97%

  • 22047-25-2

  • 251801-1G

  • 429.39CNY

  • Detail
  • Aldrich

  • (251801)  Acetylpyrazine  97%

  • 22047-25-2

  • 251801-5G

  • 1,270.62CNY

  • Detail

22047-25-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-pyrazin-2-ylethanone

1.2 Other means of identification

Product number -
Other names Methyl pyrazinyl ketone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:22047-25-2 SDS

22047-25-2Synthetic route

1,4-pyrazine
290-37-9

1,4-pyrazine

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

acetylpyrazine
22047-25-2

acetylpyrazine

Conditions
ConditionsYield
With NH4S2O8; silver nitrate; trifluoroacetic acid In dichloromethane; water at 40℃; for 2.5h;100%
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; sulfuric acid In dichloromethane; water at 40℃; Reagent/catalyst; Solvent; Minisci Aromatic Substitution;26%
1-(pyrazin-2-yl)butan-1-one
61892-81-7

1-(pyrazin-2-yl)butan-1-one

A

acetylpyrazine
22047-25-2

acetylpyrazine

B

2-Methyl-1-pyrazin-2-yl-cyclopropanol
138836-01-8, 138836-02-9

2-Methyl-1-pyrazin-2-yl-cyclopropanol

Conditions
ConditionsYield
In tert-butyl alcohol; benzene for 4h; Irradiation;A 1%
B 95%
3-acetylpyrazine N-oxide
120992-58-7

3-acetylpyrazine N-oxide

acetylpyrazine
22047-25-2

acetylpyrazine

Conditions
ConditionsYield
With Eosin Y; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 3h; Inert atmosphere; Irradiation; chemoselective reaction;90%
3-methyl-1-(pyrazin-2-yl)butan-1-one
86461-64-5

3-methyl-1-(pyrazin-2-yl)butan-1-one

A

acetylpyrazine
22047-25-2

acetylpyrazine

B

2,2-dimethyl-1-(pyrazin-2-yl)cyclopropanol
138836-03-0

2,2-dimethyl-1-(pyrazin-2-yl)cyclopropanol

Conditions
ConditionsYield
In tert-butyl alcohol; benzene for 4h; Irradiation;A 2%
B 86%
2-pyrazine carbonitrile
19847-12-2

2-pyrazine carbonitrile

methylene chloride
74-87-3

methylene chloride

acetylpyrazine
22047-25-2

acetylpyrazine

Conditions
ConditionsYield
Stage #1: methylene chloride With iodine; magnesium In tetrahydrofuran at 60℃; for 2h; Inert atmosphere;
Stage #2: 2-pyrazine carbonitrile With copper(l) chloride In tetrahydrofuran at 50℃; for 14h; Inert atmosphere;
Stage #3: With water In tetrahydrofuran Temperature; Reagent/catalyst; Solvent; Inert atmosphere;
69%
C6H6Cl2N2

C6H6Cl2N2

acetylpyrazine
22047-25-2

acetylpyrazine

Conditions
ConditionsYield
With sodium hydrogencarbonate; dimethyl sulfoxide at 80℃; for 6h;60%
1,4-pyrazine
290-37-9

1,4-pyrazine

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

A

acetylpyrazine
22047-25-2

acetylpyrazine

B

1,1′-(pyrazine-2,5-diyl)diethanone
39248-49-2

1,1′-(pyrazine-2,5-diyl)diethanone

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; formic acid; dimethyl sulfoxide In dichloromethane; water at 40℃; Catalytic behavior; Reagent/catalyst; Solvent; Minisci Aromatic Substitution;A 58%
B 10%
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; sulfuric acid In water at 50℃; Minisci Aromatic Substitution;A 26%
B 33%
1,4-pyrazine
290-37-9

1,4-pyrazine

acetaldehyde
75-07-0

acetaldehyde

acetylpyrazine
22047-25-2

acetylpyrazine

Conditions
ConditionsYield
With tert.-butylhydroperoxide; di-tert-butyl peroxide; iron(II) sulfate In dichloromethane; sulfuric acid at 5℃; for 1h;50%
2-pyrazine carbonitrile
19847-12-2

2-pyrazine carbonitrile

methyl magnesium iodide
917-64-6

methyl magnesium iodide

acetylpyrazine
22047-25-2

acetylpyrazine

Conditions
ConditionsYield
In diethyl ether at 20℃; for 1h; Addition;42%
In diethyl ether at -10 - 10℃; for 1h;40%
Stage #1: 2-pyrazine carbonitrile; methyl magnesium iodide In diethyl ether
Stage #2: With water
2-(3,3-dimethylbutyryl)pyrazine
138835-87-7

2-(3,3-dimethylbutyryl)pyrazine

acetylpyrazine
22047-25-2

acetylpyrazine

Conditions
ConditionsYield
In hexane for 20h; Irradiation;15%
In tert-butyl alcohol; benzene for 5h; Quantum yield; Irradiation;
2-pyrazine carbonitrile
19847-12-2

2-pyrazine carbonitrile

methylmagnesium bromide
75-16-1

methylmagnesium bromide

acetylpyrazine
22047-25-2

acetylpyrazine

Conditions
ConditionsYield
With diethyl ether
1,4-pyrazine
290-37-9

1,4-pyrazine

acetaldehyde
75-07-0

acetaldehyde

A

acetylpyrazine
22047-25-2

acetylpyrazine

B

1,1′-(pyrazine-2,5-diyl)diethanone
39248-49-2

1,1′-(pyrazine-2,5-diyl)diethanone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; sulfuric acid; iron(II) sulfate In water; benzene Yields of byproduct given;A 28 % Chromat.
B n/a
1H-imidazole
288-32-4

1H-imidazole

C6H5N2O(1-)*K(1+)

C6H5N2O(1-)*K(1+)

A

acetylpyrazine
22047-25-2

acetylpyrazine

B

imidazole potassium salt
20671-53-8

imidazole potassium salt

Conditions
ConditionsYield
In dimethyl sulfoxide at 24.9℃; Equilibrium constant;
pyrazinamide
98-96-4

pyrazinamide

acetylpyrazine
22047-25-2

acetylpyrazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / POCl3 / 1.5 h / 100 °C
2: 40 percent / diethyl ether / 1 h / -10 - 10 °C
View Scheme
2-pyrazine carbonitrile
19847-12-2

2-pyrazine carbonitrile

acetylpyrazine
22047-25-2

acetylpyrazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2.) H+, H2O
2: 2-methyl-propan-2-ol; benzene / 5 h / Irradiation
View Scheme
L-serin
56-45-1

L-serin

L-lysine
56-87-1

L-lysine

D-glucose
50-99-7

D-glucose

A

1,4-pyrazine
290-37-9

1,4-pyrazine

B

2-Methylpyrazine
109-08-0

2-Methylpyrazine

C

2,5-dimethyl-pyrazine
123-32-0

2,5-dimethyl-pyrazine

D

2,3-dimethylpyrazine
5910-89-4

2,3-dimethylpyrazine

E

acetylpyrazine
22047-25-2

acetylpyrazine

F

2-ethyl-3,6-dimethylpyrazine
13360-65-1

2-ethyl-3,6-dimethylpyrazine

G

2,6-dimethylpyrazine
108-50-9

2,6-dimethylpyrazine

H

2,3,5-trimethylpyrazine
14667-55-1

2,3,5-trimethylpyrazine

I

2-ethyl-6-methylpyrazine
13925-03-6

2-ethyl-6-methylpyrazine

J

2-ethyl-5-methypyrazine
13360-64-0

2-ethyl-5-methypyrazine

Conditions
ConditionsYield
In water at 130℃; for 2h; pH=8; Maillard reaction;
L-lysine
56-87-1

L-lysine

D-glucose
50-99-7

D-glucose

A

1,4-pyrazine
290-37-9

1,4-pyrazine

B

2-Methylpyrazine
109-08-0

2-Methylpyrazine

C

2,5-dimethyl-pyrazine
123-32-0

2,5-dimethyl-pyrazine

D

2,3-dimethylpyrazine
5910-89-4

2,3-dimethylpyrazine

E

acetylpyrazine
22047-25-2

acetylpyrazine

F

2-ethyl-3,6-dimethylpyrazine
13360-65-1

2-ethyl-3,6-dimethylpyrazine

G

2,6-dimethylpyrazine
108-50-9

2,6-dimethylpyrazine

H

2,3,5-trimethylpyrazine
14667-55-1

2,3,5-trimethylpyrazine

I

2-ethyl-3,5-dimethylpyrazine
13925-07-0

2-ethyl-3,5-dimethylpyrazine

J

2-ethyl-5-methypyrazine
13360-64-0

2-ethyl-5-methypyrazine

Conditions
ConditionsYield
In water at 130℃; for 2h; pH=8; Maillard reaction;
2-ethylpyrazine
13925-00-3

2-ethylpyrazine

acetylpyrazine
22047-25-2

acetylpyrazine

Conditions
ConditionsYield
With tert.-butylhydroperoxide In water at 60℃; for 12h;66 %Spectr.
acetylpyrazine
22047-25-2

acetylpyrazine

2-bromo-1-pyrazin-2-yl-ethan-1-one hydrobromide
126353-32-0

2-bromo-1-pyrazin-2-yl-ethan-1-one hydrobromide

Conditions
ConditionsYield
With pyridinium hydrobromide perbromide; hydrogen bromide In water; acetic acid at 20℃; for 0.1h;100%
With hydrogen bromide; bromine In water at 80 - 90℃; for 1h;82%
With pyridinium hydrobromide perbromide; hydrogen bromide; acetic acid at 20℃; for 1h;
With hydrogen bromide; bromine; acetic acid at 23℃; for 4h; Inert atmosphere;
acetylpyrazine
22047-25-2

acetylpyrazine

5-amino isophthaloyl hydrazide

5-amino isophthaloyl hydrazide

C20H19N9O2

C20H19N9O2

Conditions
ConditionsYield
With acetic acid In ethanol Reflux;100%
acetylpyrazine
22047-25-2

acetylpyrazine

1-(1-phenylethyl)-2-methyleneaziridine

1-(1-phenylethyl)-2-methyleneaziridine

2-pyrazin-2-yl-4-methyl-1-(1-phenylethyl)pyrrole

2-pyrazin-2-yl-4-methyl-1-(1-phenylethyl)pyrrole

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) at 120℃; for 72h;96%
Dimethyl oxalate
553-90-2

Dimethyl oxalate

acetylpyrazine
22047-25-2

acetylpyrazine

4-(2-pyrazinyl)-2,4-dioxobutanoic acid methyl ester
858599-85-6

4-(2-pyrazinyl)-2,4-dioxobutanoic acid methyl ester

Conditions
ConditionsYield
Stage #1: acetylpyrazine With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.75h;
Stage #2: Dimethyl oxalate In tetrahydrofuran for 0.166667h;
96%
acetylpyrazine
22047-25-2

acetylpyrazine

thieno[2,3-d]pyrimidin-4-ylhydrazine
14080-58-1

thieno[2,3-d]pyrimidin-4-ylhydrazine

4-(2-(1-(pyrazin-2-yl)ethylidene)hydrazinyl)thieno[2,3-d]pyrimidine

4-(2-(1-(pyrazin-2-yl)ethylidene)hydrazinyl)thieno[2,3-d]pyrimidine

Conditions
ConditionsYield
In ethanol for 24h; Reflux;96%
acetylpyrazine
22047-25-2

acetylpyrazine

2-(1-hydroxyethyl)pyrazine
94777-52-3

2-(1-hydroxyethyl)pyrazine

Conditions
ConditionsYield
Stage #1: acetylpyrazine With C27H43AlClN3Si3; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In neat (no solvent) at 20℃; for 16h;
Stage #2: With silica gel at 20℃; Catalytic behavior;
95%
With sodium tetrahydroborate In methanol Ambient temperature;
With lithium aluminium tetrahydride In diethyl ether at -78℃; for 1h;
acetylpyrazine
22047-25-2

acetylpyrazine

isoniazid
54-85-3

isoniazid

N’-(1-(pyrazin-2-yl)ethylidene)isonicotinohydrazide

N’-(1-(pyrazin-2-yl)ethylidene)isonicotinohydrazide

Conditions
ConditionsYield
With formic acid In ethanol for 4h; Reflux;95%
With formic acid In ethanol for 5h; Reflux;90%
In methanol for 4h; Reflux;64%
acetylpyrazine
22047-25-2

acetylpyrazine

ethene
74-85-1

ethene

carbon monoxide
201230-82-2

carbon monoxide

dihydro-5-methyl-5-(2-pyradinyl)-2(3H)-furanone

dihydro-5-methyl-5-(2-pyradinyl)-2(3H)-furanone

Conditions
ConditionsYield
dodecacarbonyl-triangulo-triruthenium In toluene at 140℃; for 20h;94%
acetylpyrazine
22047-25-2

acetylpyrazine

2-benzyl-3-hydroxy-2,3-dihydro-isoindol-1-one
17448-14-5

2-benzyl-3-hydroxy-2,3-dihydro-isoindol-1-one

2-benzyl-3-(2-oxo-2-(pyrazin-2-yl)ethyl)isoindolin-1-one

2-benzyl-3-(2-oxo-2-(pyrazin-2-yl)ethyl)isoindolin-1-one

Conditions
ConditionsYield
With Sn(4+)*4C2F6NO4S2(1-)*8C2H6OS In toluene at 110℃; for 24h; Inert atmosphere; Sealed tube;94%
acetylpyrazine
22047-25-2

acetylpyrazine

4-bromophenylhydrazine hydrochloride
622-88-8

4-bromophenylhydrazine hydrochloride

2-acetylpyrazine 4-bromophenylhydrazone

2-acetylpyrazine 4-bromophenylhydrazone

Conditions
ConditionsYield
With sodium acetate In ethanol; chloroform for 12h; Ambient temperature;93.5%
acetylpyrazine
22047-25-2

acetylpyrazine

1,3-benzothiazol-2-ylhydrazine
615-21-4

1,3-benzothiazol-2-ylhydrazine

N-Benzothiazol-2-yl-N'-[1-pyrazin-2-yl-eth-(E)-ylidene]-hydrazine

N-Benzothiazol-2-yl-N'-[1-pyrazin-2-yl-eth-(E)-ylidene]-hydrazine

Conditions
ConditionsYield
With acetic acid In methanol at 80℃;93%
acetylpyrazine
22047-25-2

acetylpyrazine

picolinic acid hydrazide
1452-63-7

picolinic acid hydrazide

N′-(1-(pyrazin-2-yl)ethylidene)picolinohydrazide

N′-(1-(pyrazin-2-yl)ethylidene)picolinohydrazide

Conditions
ConditionsYield
With formic acid In ethanol for 5h; Reflux;93%
In ethanol
acetylpyrazine
22047-25-2

acetylpyrazine

C6H8N2O

C6H8N2O

Conditions
ConditionsYield
Stage #1: acetylpyrazine With trimethylaluminum; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; 3,3'-bis-(3,5-bis-trifluoromethyl-phenyl)-[1,1']binaphthalenyl-2,2'-diol In toluene at 20℃; for 2h; Glovebox; Inert atmosphere;
Stage #2: With methanol for 0.5h; enantioselective reaction;
93%
pent-4-en-2-ynyl-carbamic acid tert-butyl ester

pent-4-en-2-ynyl-carbamic acid tert-butyl ester

acetylpyrazine
22047-25-2

acetylpyrazine

[2-(1-hydroxy-1-pyrazin-2-yl-ethyl)-penta-2,4-dienyl]-carbamic acid tert-butyl ester

[2-(1-hydroxy-1-pyrazin-2-yl-ethyl)-penta-2,4-dienyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With (R)-xylyl-WALPHOS; triphenylacetic acid; hydrogen; bis(cycloocta-1,5-diene)rhodium(I) trifluoromethanesulfonate In 1,2-dichloro-ethane at 40℃; under 760 Torr;92%
acetylpyrazine
22047-25-2

acetylpyrazine

C9H6F3NO2

C9H6F3NO2

(S)-4,4,4-trifluoro-3-(nitromethyl)-3-phenyl-1-(pyrazin-2-yl)butan-1-one

(S)-4,4,4-trifluoro-3-(nitromethyl)-3-phenyl-1-(pyrazin-2-yl)butan-1-one

Conditions
ConditionsYield
Stage #1: acetylpyrazine With bis(acetylacetonate)nickel(II); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) In isopropyl alcohol at 0℃; for 0.5h; Michael Addition; Schlenk technique; Inert atmosphere;
Stage #2: C9H6F3NO2 In isopropyl alcohol at 0℃; for 96h; Michael Addition; Schlenk technique; Inert atmosphere; enantioselective reaction;
92%
acetylpyrazine
22047-25-2

acetylpyrazine

C18H12ClF3N2O4S

C18H12ClF3N2O4S

(S)-3-(5-chloro-1-tosyl-1H-indol-3-yl)-4,4,4-trifluoro-3-(nitromethyl)-1-(pyrazin-2-yl)butan-1-one

(S)-3-(5-chloro-1-tosyl-1H-indol-3-yl)-4,4,4-trifluoro-3-(nitromethyl)-1-(pyrazin-2-yl)butan-1-one

Conditions
ConditionsYield
With C28H29N3O; cobalt(II) aceylacetonate In tert-butyl methyl ether at 20℃; Michael Addition; Schlenk technique; Inert atmosphere; enantioselective reaction;92%
acetylpyrazine
22047-25-2

acetylpyrazine

5-Iodoisophthalic dihydrazide
193614-92-5

5-Iodoisophthalic dihydrazide

C20H17IN8O2

C20H17IN8O2

Conditions
ConditionsYield
With acetic acid In ethanol Reflux;92%
acetylpyrazine
22047-25-2

acetylpyrazine

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

3-(N,N-dimethylamino)-1-(pyrazin-2-yl)prop-2-en-1-one
866000-17-1

3-(N,N-dimethylamino)-1-(pyrazin-2-yl)prop-2-en-1-one

Conditions
ConditionsYield
With guanidineacetic acid at 100℃; for 1h;91%
With L-proline In neat (no solvent) at 80℃; for 1.5h;90%
With triethylamine at 110℃; for 16h;81%
acetylpyrazine
22047-25-2

acetylpyrazine

trans-1-(4-fluorophenyl)-2-nitro-ethene
706-08-1, 5153-69-5

trans-1-(4-fluorophenyl)-2-nitro-ethene

(R)-3-(4-fluorophenyl)-4-nitro-1-(pyrazin-2-yl)butan-1-one
1433955-80-6

(R)-3-(4-fluorophenyl)-4-nitro-1-(pyrazin-2-yl)butan-1-one

Conditions
ConditionsYield
With nickel(II) acetate tetrahydrate; (4R,4'R,5S,5'S)-2,2'-(propane-2,2-diyl)bis(4,5-diphenyl-4,5-dihydrooxazole) In isopropyl alcohol at 20℃; for 3h; Michael Addition; Inert atmosphere; enantioselective reaction;91%
2-Aminonicotinaldehyde
7521-41-7

2-Aminonicotinaldehyde

acetylpyrazine
22047-25-2

acetylpyrazine

2-(pyrazin-2-yl)-1,8-naphthyridine
1338090-17-7

2-(pyrazin-2-yl)-1,8-naphthyridine

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 60℃;91%
With potassium hydroxide In methanol at 60℃; Inert atmosphere; Schlenk technique; Reflux;85%
acetylpyrazine
22047-25-2

acetylpyrazine

2,5-dihydroxybenzohydrazide
15791-90-9

2,5-dihydroxybenzohydrazide

N1-(2,5-dihydroxybenzoyl)-N2-[1-(2-pyrazinyl)ethylidene]hydrazine

N1-(2,5-dihydroxybenzoyl)-N2-[1-(2-pyrazinyl)ethylidene]hydrazine

Conditions
ConditionsYield
With acetic acid In ethanol for 1h; Reflux;91%
acetylpyrazine
22047-25-2

acetylpyrazine

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

malononitrile
109-77-3

malononitrile

2-amino-4-(3,4-dimethoxyphenyl)-6-(pyrazin-2-yl)nicotinonitrile

2-amino-4-(3,4-dimethoxyphenyl)-6-(pyrazin-2-yl)nicotinonitrile

Conditions
ConditionsYield
With ammonium acetate In ethanol Reflux;91%
acetylpyrazine
22047-25-2

acetylpyrazine

5-methoxy isophthaloyl hydrazide
23341-07-3

5-methoxy isophthaloyl hydrazide

C21H20N8O3

C21H20N8O3

Conditions
ConditionsYield
With acetic acid In ethanol Reflux;91%
acetylpyrazine
22047-25-2

acetylpyrazine

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

3-dimethylamino-1-(3-pyrazinyl)-2-propene-1-one
111781-53-4

3-dimethylamino-1-(3-pyrazinyl)-2-propene-1-one

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 20h; Inert atmosphere; Schlenk technique;90.2%
In xylene Heating;73%
In methanol for 10h; Reflux;38%
for 19h; Heating / reflux;
Reflux;
acetylpyrazine
22047-25-2

acetylpyrazine

C10H5F6NO2

C10H5F6NO2

(S)-4,4,4-trifluoro-3-(4-(trifluoromethyl)phenyl)-3-(nitromethyl)-1-(pyrazin-2-yl)butan-1-one

(S)-4,4,4-trifluoro-3-(4-(trifluoromethyl)phenyl)-3-(nitromethyl)-1-(pyrazin-2-yl)butan-1-one

Conditions
ConditionsYield
Stage #1: acetylpyrazine With bis(acetylacetonate)nickel(II); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) In isopropyl alcohol at 0℃; for 0.5h; Michael Addition; Schlenk technique; Inert atmosphere;
Stage #2: C10H5F6NO2 In isopropyl alcohol at 0℃; Michael Addition; Schlenk technique; Inert atmosphere; enantioselective reaction;
90%
pyridine
110-86-1

pyridine

acetylpyrazine
22047-25-2

acetylpyrazine

N-{1-pyrazinyl-1-oxo-2-ethyl}pyridinium iodide

N-{1-pyrazinyl-1-oxo-2-ethyl}pyridinium iodide

Conditions
ConditionsYield
With iodine at 110℃; for 3h;88%
With iodine for 1h; Reflux;82%
With iodine at 90℃; for 1.5h;48%
acetylpyrazine
22047-25-2

acetylpyrazine

benzil dihydrazone
4702-78-7

benzil dihydrazone

N',N'-bis[1-(pyrazine-2-yl)ethylidene]benzil dihydrazone

N',N'-bis[1-(pyrazine-2-yl)ethylidene]benzil dihydrazone

Conditions
ConditionsYield
for 5h; Heating;87%

22047-25-2Relevant articles and documents

Novel thiosemicarbazones derived from formyl- and acyldiazines: Synthesis, effects on cell proliferation, and synergism with antiviral agents

Easmon,Heinisch,Holzer,Rosenwirth

, p. 3288 - 3296 (1992)

The synthesis of a series of novel thiosemicarbazones (TSC's) derived from various alkyl diazinyl (3-pyridazinyl, 4-pyrimidinyl, 2-pyrazinyl) ketones and 3-pyridazinecarbaldehyde and their evaluation against herpes simplex virus (HSV) and human immunodeficiency virus (HIV) as well as the determination of their cytotoxicity are described. In addition, the effects of combination of such TSC's with the well-known antiviral drugs acyclovir (ACV) and 3'-azido-3'-deoxythymidine (AZT) were studied. Under our experimental conditions, i.e. determination of virus-induced cytopathic effect upon infection of HUT78 cells with HSV-1 and upon infection of MT4 cells with HIV-1, no antiviral activity could be detected with any of the TSC's. However, pronounced effects on proliferation of these rapidly growing T4 lymphocyte cell lines were observed. Clear structure-activity relationships with regard to these cytotoxic effects could be established: compared to pyridine, pyrazine, or pyrimidine-derived TSC's most of the 3- pyridazinyl congeners investigated are less cytotoxic: introduction of a methyl group into C-6 of the pyridazine system or prolongation of the acyl moiety in these compounds has essentially no influence; all compounds bearing an N,N-dimethylamino or a cycloamino substituent are much more toxic than those with an NH2 or NHR substituent; the nature of R in the latter type of compounds has only moderate influence. It has been reported that combination of TSC's with the antiviral agent acyclovir (ACV) results in potentiation of this well-known drug. We evaluated the potential of our series of novel TSC's in combination with ACV for inhibition of HSV-1-induced cytopathic effect in HUT78 cells and in combination with 3'-azido-3'-deoxythymidine (AZT) for inhibition of HIV-1-induced cytopathic effect in MT4 cells. Only four compounds out of this series, all characterized by an unsubstituted NH2 group, exhibited moderate synergism with the above mentioned antiviral drugs. Our results do not support the previously expressed opinion that TSC's are selective antiviral agents. In our test systems no evidence for inhibition of virus-induced cytopathic effect was obtained. The TSC derivatives exhibited a broad range of cytotoxic effects, some at concentrations considerably below those reported to have antiviral efficacy. Several of our novel diazine- derived compounds proved advantageous over the previously described pyridine analogues with regard to cytotoxicity. Moderate synergism could be detected for relatively noncytotoxic TSC's with the antiviral drugs ACV (antiherpes) and AZT (anti-HIV).

Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions

Kim, Se Hyun,An, Ju Hyeon,Lee, Jun Hee

supporting information, p. 3735 - 3742 (2021/05/04)

Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is

Method for synthesizing 2-acetyl pyrazine

-

Paragraph 0022-0029, (2019/06/27)

The invention relates to the field of chemical organic synthesis, in particular to a method for synthesizing 2-acetyl pyrazine. The method comprises the following steps: (1) preparation of a Grignardreagent: adding metallic magnesium, an anhydrous polar solvent, elemental iodine and methyl chloride into a pressure vessel, and stirring to prepare the Grignard reagent; (2) adding reaction: adding 2-cyanopyrazine, tetrahydrofuran, a catalyst and the Grignard reagent into a reactor, and refluxing and condensing to obtain an intermediate product; (3) hydrolyzing: adding water into the intermediateproduct, adjusting the pH value by using dilute acid, stirring and refluxing, and then adjusting to be neutral; and finally, extracting with toluene; and (4) aftertreatment: desolventizing a tolueneextracting solution, dissolving desolventized solid with ethanol, adding activated carbon, filtering, and cooling to obtain a white solid P1; and recrystallizing with the ethanol to obtain the 2-acetylpyrazine. According to the method, a monovalent copper salt is adopted as a catalyst, the yield of 2-acetylpyrazine is increased to be 69%, meanwhile, the reaction speed is increased, and the synthesis reaction temperature is also reduced.

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