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4940-11-8 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 4940-11-8 differently. You can refer to the following data:
1. White crystalline solid with characteristic, very sweet, caramel-like odor and taste. In dilute solution it possesses a sweet, fruitlike flavor and odor.
2. It forms white crystals (mp 90–91°C) with very sweet caramel-like odor, four to six times more potent than maltol. Several syntheses have been developed for its preparation. In a one-pot process, for example, ??-ethylfurfuryl alcohol is treated with halogen to give 4-halo- 6-hydroxy-2-ethyl-2H-pyran-3(6H)-one, which need not be isolated and can be converted to ethylmaltol by aqueous hydrolysis
3. Ethyl maltol has a very sweet, fruit-like odor of immense tenacity and sweet, fruity taste with initial bitter-tart flavor; rapid loss of flavor per se. It is four to six times more potent than maltol.

Occurrence

Has apparently not been reported to occur in nature.

History

In 1891, Bernhardi first discovered synthesis, and its derivatives are used for therapeutic purposes and can be prepared in industrial experiments. As war ammunition, it was first used by France in fortress warfare, and was prepared before the war. In October 1914, the French used it as a gas grenade, planned for the fortress battle. On January 7, 1915, it was actually used in the forest of Argonnen on the western front of France.

Uses

Different sources of media describe the Uses of 4940-11-8 differently. You can refer to the following data:
1. Ethyl Maltol is an extract from medicinal plants such as P. Incarnata and can be used as an anticonvulsant, acting as a depressant, and on motor activity.
2. Ethyl Maltol is a flavoring agent that is a white, crystalline powder. it has a unique odor and a sweet taste that resembles fruit. the melt- ing point is 90°c. it is sparingly soluble in water and propylene gly- col and soluble in alcohol and chloroform. it is obtained by chemical synthesis.
3. Flavor and fragrance enhancer in foods, especially baked goods, beverages, and synthetic berry and citrus flavorings; minimizes undesirable flavors in tobacco products, cough syrup, vitamins, cosmetics, and saccharin-containing products.

Preparation

Different sources of media describe the Preparation of 4940-11-8 differently. You can refer to the following data:
1. Several syntheses have been developed for its preparation. In a one-pot process, for example, ??-ethylfurfuryl alcohol is treated with halogen to give 4-halo- 6-hydroxy-2-ethyl-2H-pyran-3(6H)-one, which need not be isolated and can be converted to ethylmaltol by aqueous hydrolysis.
2. Fermentation method. Kojic acid is obtained from starch fermentation, and then ethyl maltol is obtained by etherification, oxidation, debenzylation, decarboxylation, hydroxylation and reduction. Pyrofuroic acid method. A solution of pyrofuroic acid and acetic acid at a temperature of 90°C was added dropwise to the ether solution of diacetyl peroxide within 1~2h, and then the mixture was raised to 2h within 2h. 110 ° C, so that the 2-position of pyrofuroic acid can be directly alkylated to obtain ethyl maltol. furfuryl alcohol method. Furfuryl alcohol is chlorinated in methanol aqueous solution by introducing chlorine gas to generate 4-chloro-3-hydroxy-4H-ketone, and then heated and hydrolyzed to obtain pyrofuroic acid; under alkaline conditions, pyrofuroic acid is condensed with acetaldehyde to obtain hydroxyethyl Pyrofuroic acid, which is reduced to ethyl maltol with zinc powder in hydrochloric acid. Furfural method. Furfural reacts with ethylmagnesium bromide to obtain ethylfurfuryl alcohol (α-furan alkanol), which is then oxidized by chlorine gas in methanol aqueous solution at 0°C, and then heated to 100°C for hydrolysis to obtain ethyl maltol.

Production Methods

Unlike maltol, ethyl maltol does not occur naturally. It may be prepared by treating a-ethylfurfuryl alcohol with a halogen to produce 4-halo-6-hydroxy-2-ethyl-2H-pyran-3(6H)-one, which is converted to ethyl maltol by hydrolysis.

Taste threshold values

Taste characteristics at 70 ppm: sweet, burnt cotton, sugar candy-like with jamy, strawberry notes.

General Description

Ethyl maltol is a synthetic homologue of maltol, often found as flavor enhancers and it contributes to the fragrance of commercials products such as cereals, breads, malt beverages, coffee, soybeans and chocolate milk.

Flammability and Explosibility

Notclassified

Pharmaceutical Applications

Ethyl maltol is used in pharmaceutical formulations and food products as a flavoring agent or flavor enhancer in applications similar to maltol. It has a flavor and odor 4–6 times as intense asmaltol. Ethyl maltol is used in oral syrups at concentrations of about 0.004% w/v and also at low levels in perfumery.

Safety Profile

Moderately toxic by ingestion and subcutaneous routes. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Safety

In animal feeding studies, ethyl maltol has been shown to be well tolerated with no adverse toxic, reproductive, or embryogenic effects. It has been reported that while the acute toxicity of ethyl maltol, in animal studies, is slightly greater than maltol, with repeated dosing the opposite is true. The WHO has set an acceptable daily intake for ethyl maltol at up to 2 mg/kg bodyweight. LD50 (chicken, oral): 1.27 g/kg LD50 (rat, oral): 1.15 g/kg LD50 (mouse, oral): 0.78 g/kg LD50 (mouse, SC): 0.91 g/kg

Synthesis

From kojic acid

Metabolism

When orally administered, ethyl maltol was rapidly and extensively absorbed. Elimination was also extensive and rapid, involving conjugation as the glucuronide and ethereal sulphate, and excretion in the urine to the extent of 65-70% within 24 hr. Rate studies after iv dosage indicated that the bulk (86%) of the recovered conjugates was excreted within 6 hr (Rennhard, 1971).

storage

Solutions may be stored in glass or plastic containers. The bulk material should be stored in a well-closed container, protected from light, in a cool, dry place.

Regulatory Status

GRAS listed. Included in the FDA Inactive Ingredients Database (oral syrup).

Check Digit Verification of cas no

The CAS Registry Mumber 4940-11-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,9,4 and 0 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 4940-11:
(6*4)+(5*9)+(4*4)+(3*0)+(2*1)+(1*1)=88
88 % 10 = 8
So 4940-11-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3

4940-11-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Sigma-Aldrich

  • (PHR1267)  Ethylmaltol  pharmaceutical secondary standard; traceable to USP

  • 4940-11-8

  • PHR1267-1G

  • 732.19CNY

  • Detail
  • Aldrich

  • (412929)  2-Ethyl-3-hydroxy-4H-pyran-4-one  99%

  • 4940-11-8

  • 412929-25G

  • 761.67CNY

  • Detail
  • Aldrich

  • (412929)  2-Ethyl-3-hydroxy-4H-pyran-4-one  99%

  • 4940-11-8

  • 412929-100G

  • 1,875.51CNY

  • Detail
  • USP

  • (1266008)  Ethylmaltol  United States Pharmacopeia (USP) Reference Standard

  • 4940-11-8

  • 1266008-1G

  • 4,326.66CNY

  • Detail

4940-11-8SDS

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 2-Ethyl-3-hydroxy-4H-pyran-4-one

1.2 Other means of identification

Product number -
Other names Ethyl Maltol

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:4940-11-8 SDS

4940-11-8Synthetic route

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

Conditions
ConditionsYield
With chlorine In methanol; water 1.) -5 deg C; 2.) 90-95 deg C, 3.5 h;67%
With chlorine In methanol; water at 90 - 95℃; for 3.5h; Rearrangement;67%
Stage #1: ethylfurfuryl alcohol With oxygen In methanol at 93℃; Molecular sieve;
Stage #2: With oxygen In methanol at 20℃; for 2h;
Stage #3: With hydrogenchloride In water at 100℃; for 2h; pH=2.5 - 3; Solvent; Temperature;
66.8%
With tert-butylhypochlorite In acetic acid65%
hydroxyethyl maltol

hydroxyethyl maltol

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

Conditions
ConditionsYield
With hydrogenchloride; zinc In ethanol at 55℃; for 3h; Temperature;
3-hydroxy-2-ethyl-4H-thiopyran-4-thione

3-hydroxy-2-ethyl-4H-thiopyran-4-thione

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

Conditions
ConditionsYield
With Lawessons reagent In 1,4-dioxane for 1h; Heating;
furfural
98-01-1

furfural

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogen / water / 8 h / 90 °C / 15001.5 Torr
2: chlorine / water; methanol / -5 - 60 °C
3: sodium hydroxide / 3 h / 55 °C
4: zinc; hydrogenchloride / ethanol / 3 h / 55 °C
View Scheme
(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: chlorine / water; methanol / -5 - 60 °C
2: sodium hydroxide / 3 h / 55 °C
3: zinc; hydrogenchloride / ethanol / 3 h / 55 °C
View Scheme
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

benzyl bromide
100-39-0

benzyl bromide

3-(benzyloxy)-2-ethyl-4H-pyran-4-one
111782-87-7

3-(benzyloxy)-2-ethyl-4H-pyran-4-one

Conditions
ConditionsYield
In acetone for 6h; Reflux;98%
Stage #1: 2-ethyl-3-hydroxy-4-pyranone With sodium hydroxide In methanol Heating;
Stage #2: benzyl bromide In methanol for 6h; Heating; Further stages.;
85%
With sodium hydroxide In ethanol Heating;80%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

benzenesulfonic acid
98-11-3

benzenesulfonic acid

3,4-dihydroxy-2-ethylpyrylium benzenesulfonate

3,4-dihydroxy-2-ethylpyrylium benzenesulfonate

Conditions
ConditionsYield
In methanol for 1h; Reflux;98%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

salicylic acid
69-72-7

salicylic acid

2-ethyl-3-hydroxy-4-pyrone/salicylic acid 1:1 cocrystals
1325228-63-4

2-ethyl-3-hydroxy-4-pyrone/salicylic acid 1:1 cocrystals

Conditions
ConditionsYield
In methanol at 64℃; for 1h;98%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

methyl iodide
74-88-4

methyl iodide

2-ethyl-3-methoxy-4Hpyran-4-one
50741-69-0

2-ethyl-3-methoxy-4Hpyran-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 4h; Inert atmosphere; Reflux;97%
With potassium carbonate In acetone at 25℃; for 4h;93%
With potassium carbonate In acetone for 8h; Reflux;
dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer

dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

sodium methylate
124-41-4

sodium methylate

Rh(C5(CH3)5)Cl(C5H2O3C2H5)
173413-66-6

Rh(C5(CH3)5)Cl(C5H2O3C2H5)

Conditions
ConditionsYield
In methanol byproducts: NaCl; N2-atmosphere; stoich. amts., refluxing for 3 h; solvent removal, extn. into CH2Cl2, filtration (Celite), evapn., recrystn. (CH2Cl2/light petroleum);96%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

titanium tetrachloride
7550-45-0

titanium tetrachloride

bis-ethylmaltoldichloro-titanium(IV)

bis-ethylmaltoldichloro-titanium(IV)

Conditions
ConditionsYield
In tetrahydrofuran ethylmaltol stirred with anhyd. THF at room temp., TiCl4 added dropwise to soln., stirred at room. temp for 30 min; filtered, washed with Et2O, recrystd. from CH2Cl2-petroleum ether (1:1);95%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

{(η6-1,3,5-Me3C6H3)RuCl2}2

{(η6-1,3,5-Me3C6H3)RuCl2}2

sodium methylate
124-41-4

sodium methylate

(C6(CH3)3H3)RuCl(OOC5H2C2H5O)
151781-33-8

(C6(CH3)3H3)RuCl(OOC5H2C2H5O)

Conditions
ConditionsYield
In methanol; water byproducts: NaCl; Sodium methoxide and ethylmaltol are added to a suspn. of the Ru-compd. in CH3OH/H2O and the mixt. is refluxed for 2 h.; The solvent is removed. The residue is dissolved in CH2Cl2. After filtn. the solvent is evaporated, recrystn. from CH2Cl2/diethylether, elem. anal.;80%
zinc(II) sulfate heptahydrate

zinc(II) sulfate heptahydrate

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

C14H14O6Zn
98445-51-3

C14H14O6Zn

Conditions
ConditionsYield
Stage #1: 2-ethyl-3-hydroxy-4-pyranone With lithium hydroxide monohydrate In water at 20℃; for 0.5h;
Stage #2: zinc(II) sulfate heptahydrate In water at 20℃; for 5h;
77%
vanadyl sulfate trihydrate

vanadyl sulfate trihydrate

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

bis(ethylmaltolato)(ethylmaltol)oxovanadium(IV) monohydrate

bis(ethylmaltolato)(ethylmaltol)oxovanadium(IV) monohydrate

Conditions
ConditionsYield
In water VOSO4*3H2O and ethylmaltol (molar ratio 1:2) suspended in water at 45°C; pptd. over 15-20 min; cooled to room temp.; filtered; ppt. air dried; elem. anal.;72%
oxovanadium(IV) sulfate

oxovanadium(IV) sulfate

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

salicylaldehyde
90-02-8

salicylaldehyde

anthranilic acid hydrazide
1904-58-1

anthranilic acid hydrazide

C21H18N3O6V

C21H18N3O6V

Conditions
ConditionsYield
Stage #1: salicylaldehyde; anthranilic acid hydrazide In methanol for 0.5h;
Stage #2: oxovanadium(IV) sulfate; 2-ethyl-3-hydroxy-4-pyranone In methanol for 0.5h;
72%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

4-tert-Butylaniline
769-92-6

4-tert-Butylaniline

1-(4-(tert-butyl)phenyl)-2-ethyl-3-hydroxypyridin-4(1H)-one

1-(4-(tert-butyl)phenyl)-2-ethyl-3-hydroxypyridin-4(1H)-one

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 160℃; for 12h; pH=5; Autoclave;70%
lanthanum(III) nitrate hexahydrate

lanthanum(III) nitrate hexahydrate

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

La(ethylmaltol(1-))3
960499-98-3

La(ethylmaltol(1-))3

Conditions
ConditionsYield
With triethylamine In ethanol Ln(NO3)*6H2O was added to soln. ligand in EtOH and heated until ligand completely dissolved, Et3N was added and stirred for 18-24 h; ppt. was filtered, washed with cold water and cold MeOH and dried in vacuo; elem. anal.;68%
bis(acetylacetonate)oxovanadium
3153-26-2

bis(acetylacetonate)oxovanadium

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

2-chloro-N′-(3-ethoxy-2-hydroxybenzylidene)benzohydrazide

2-chloro-N′-(3-ethoxy-2-hydroxybenzylidene)benzohydrazide

C23H20ClN2O7V

C23H20ClN2O7V

Conditions
ConditionsYield
Stage #1: bis(acetylacetonate)oxovanadium; 2-ethyl-3-hydroxy-4-pyranone; 2-chloro-N′-(3-ethoxy-2-hydroxybenzylidene)benzohydrazide In methanol at 20℃; for 0.5h;
Stage #2: With air In methanol
68%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

Sn(ethylmaltol)2
361148-46-1

Sn(ethylmaltol)2

Conditions
ConditionsYield
In toluene a soln. of hydroxyketone in toluene was added a stirred soln. of Sn-compound in toluene under N2, the soln. was stirred for 2 h then left at room temp.; elem. anal.;66%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

2-ethyl-3-hydroxy-5-bromo-4H-pyran-4-one
95790-62-8

2-ethyl-3-hydroxy-5-bromo-4H-pyran-4-one

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 95℃; for 18h; Inert atmosphere;66%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 95℃; Inert atmosphere; Schlenk technique;32%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 95℃; for 18h; Inert atmosphere; Schlenk technique;
oxovanadium(IV) sulfate

oxovanadium(IV) sulfate

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

2-hydroxy-3-bromobenzaldehyde
1829-34-1

2-hydroxy-3-bromobenzaldehyde

3-hydroxybenzoic hydrazide
5818-06-4

3-hydroxybenzoic hydrazide

C21H16BrN2O7V

C21H16BrN2O7V

Conditions
ConditionsYield
Stage #1: 2-hydroxy-3-bromobenzaldehyde; 3-hydroxybenzoic hydrazide In methanol for 0.5h;
Stage #2: oxovanadium(IV) sulfate; 2-ethyl-3-hydroxy-4-pyranone In methanol for 0.5h;
65%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

europium(III) nitrate hexahydrate

europium(III) nitrate hexahydrate

Eu(ethylmaltol(1-))3*2.5H2O

Eu(ethylmaltol(1-))3*2.5H2O

Conditions
ConditionsYield
With triethylamine In ethanol Ln(NO3)*6H2O was added to soln. ligand in EtOH and heated until ligand completely dissolved, Et3N was added and stirred for 18-24 h; ppt. was filtered, washed with cold water and cold MeOH and dried in vacuo; elem. anal.;64%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

benzyl chloride
100-44-7

benzyl chloride

ethanolamine
141-43-5

ethanolamine

3-Benzyloxy-1,2-diethyl-1H-pyridin-4-one

3-Benzyloxy-1,2-diethyl-1H-pyridin-4-one

Conditions
ConditionsYield
Stage #1: 2-ethyl-3-hydroxy-4-pyranone; benzyl chloride With sodium hydroxide In methanol; ethanol; water
Stage #2: ethanolamine With sodium hydroxide In methanol; ethanol; water
63%
Stage #1: 2-ethyl-3-hydroxy-4-pyranone; benzyl chloride With sodium hydroxide In methanol; water
Stage #2: ethanolamine With sodium hydroxide In ethanol; water
63%
bis(acetylacetonate)oxovanadium
3153-26-2

bis(acetylacetonate)oxovanadium

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

N′-(3-ethoxy-2-hydroxybenzylidene)pivalohydrazide

N′-(3-ethoxy-2-hydroxybenzylidene)pivalohydrazide

C21H25N2O7V

C21H25N2O7V

Conditions
ConditionsYield
In methanol at 20℃; for 0.5h;62%

4940-11-8Relevant articles and documents

Maltol and homolog preparation method by means of molecular oxygen oxidation

-

Paragraph 0023-0027; 0053-0057, (2017/09/26)

The invention provides a maltol and homolog preparation method by means of molecular oxygen oxidation. The method comprises the following steps of charging, a first-stage oxidation reaction, a second-stage oxidation reaction and hydrolysis. According to the first-stage oxidation reaction, alpha-furyl alcohol is used as a raw material, gas with an oxygen content of 15%-85% is used as an oxidizing agent, a heteroatom molecular sieve and basic resin are used as a composite catalyst in a solvent, and an oxidizing ring opening rearrangement reaction is conducted at the temperature of 50-160 DEG C; according to the second-stage oxidation reaction, the temperature drops to 10-40 DEG C, gas with an oxygen content of 90% or above is pumped in, an epoxidation reaction is conducted, and the temperature of the reaction is kept for 0.5-3 h. According to the method, the production yield reaches 50% or above, and the production yield reaches 67% or above in the condition of optimization; the oxidation reaction conducted by using molecular oxygen has the advantages of energy conservation, low cost and environmental protection, and recycling and application of the catalysts are easier to achieve by means of the composite catalyst made from the heteroatom molecular sieve and the basic resin.

A novel heterocyclic atom exchange reaction with Lawesson's reagent: A one-pot synthesis of dithiomaltol

Brayton, Daniel,Jacobsen, Faith E.,Cohen, Seth M.,Farmer, Patrick J.

, p. 206 - 208 (2008/02/07)

A one-pot reaction of maltol with Lawesson's reagent generates dithiomaltol, a thiopyran-4-thione, via an unusual heterocyclic atom exchange (HCAE) reaction; only pyrones with proton or aliphatic substituents undergo the HCAE substitution. The Royal Society of Chemistry 2006.

OXIDATIVE REARRANGEMENT OF FURYLCARBINOLS TO 6-HYDROXY-2H-PYRAN-3(6H)-ONES, A USEFUL SYNTHON FOR THE PREPARATION OF A VARIETY OF HETEROCYCLIC COMPOUNDS. A REVIEW

Georgiadis, Minas P.,Albizati, Kim F.,Georgiadis, Taxiarchis M.

, p. 95 - 118 (2007/10/03)

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