e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Naphthoquinone Antimalarials. IV-XI. Synthesis1

LF Fieser, E Berliner, FJ Bondhus…

Index: Fieser et al. Journal of the American Chemical Society, 1948 , vol. 70, p. 3177

Full Text: HTML

Citation Number: 53

Abstract

The synthesis of 3-alkyl or aralkyl derivatives of 2-hydroxy-l, 4-naphthoquinone has been accomplished by condensation of the hydroxyquinone with an aldehyde and hydrogenation of the resulting 3-a-alkenyl derivative, 2 by the action of an allylic or benzyl halide on the hydroxyquinone silver salt to produce 3-derivatives either by direct C-alkylation or by rearrangement of an allylic ether, 3f4 and, in a few special cases, by condensation of the ...

2-Hydroxy-1,4-naphoquinone Structure

2-Hydroxy-1,4-n...

~%

4-hydroxy-3-(4-phenylphenyl)naphthalene-1,2-dione Structure

4-hydroxy-3-(4-...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

4-hydroxy-3-(4-phenylphenyl)naphthalene-1,2-dione Structure

4-hydroxy-3-(4-...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

4-hydroxy-3-(4-phenylphenyl)naphthalene-1,2-dione Structure

4-hydroxy-3-(4-...

ETHYLENE OXIDE Structure

~%

3-PROPYL-1-HEXANOL Structure

3-PROPYL-1-HEXANOL

naphthalene-1,2,4-triol Structure

naphthalene-1,2...

Cyclohexene Structure

~%

parvaquone Structure

2-Hydroxy-1,4-naphoquinone Structure

2-Hydroxy-1,4-n...

~%

parvaquone Structure

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

parvaquone Structure

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

parvaquone Structure

Ethanol Structure

1a-cyclohexyl-1a,7a-dihydronaphth[2,3b]oxirene-2,7-dione Structure

1a-cyclohexyl-1...

Sodium Methylate Structure

Sodium Methylate

~%

2-Hydroxy-1,4-naphoquinone Structure

2-Hydroxy-1,4-n...

Detail

2-Hydroxy-1,4-naphoquinone Structure

2-Hydroxy-1,4-n...

~%

3-(3-(3-Cyclohexylphenyl)propyl)-2-hydroxynaphthalene-1,4-dione Structure

3-(3-(3-Cyclohe...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

3-(3-(3-Cyclohexylphenyl)propyl)-2-hydroxynaphthalene-1,4-dione Structure

3-(3-(3-Cyclohe...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

3-(3-(3-Cyclohexylphenyl)propyl)-2-hydroxynaphthalene-1,4-dione Structure

3-(3-(3-Cyclohe...

Ethanol Structure

~%

SL 11039 Structure

Hydrochloric acid Structure

Hydrochloric acid

(3,4-dioxonaphthalen-1-yl)cyanamide Structure

(3,4-dioxonapht...

~%

SL 11039 Structure

2-isopentyl-naphthalene Structure

2-isopentyl-nap...

~%

1,4-Naphthalenedione,2-(3-methylbutyl)- Structure

1,4-Naphthalene...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

4-hydroxy-3-pentadecyl-naphthalene-1,2-dione Structure

4-hydroxy-3-pen...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

4-hydroxy-3-pentadecyl-naphthalene-1,2-dione Structure

4-hydroxy-3-pen...

Palmitoyl chloride Structure

Palmitoyl chloride

~%

4-hydroxy-3-pentadecyl-naphthalene-1,2-dione Structure

4-hydroxy-3-pen...

Ethyl6-chloro-6-oxohexanoate(ThiocticAcidImpurity) Structure

Ethyl6-chloro-6...

Bromobenzene Structure

~%

ethyl 6-(4-bromophenyl)-6-oxohexanoate Structure

ethyl 6-(4-brom...

3-(3-Trifluoromethylphenyl)propionic acid Structure

3-(3-Trifluorom...

~%

3-(3-(trifluoromethyl)phenyl)propanamide Structure

3-(3-(trifluoro...

3-(3-(trifluoromethyl)phenyl)propanoyl chloride Structure

3-(3-(trifluoro...

~%

3-(3-(trifluoromethyl)phenyl)propanamide Structure

3-(3-(trifluoro...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

Lawsone methyl ether Structure

Lawsone methyl ether

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

Lawsone methyl ether Structure

Lawsone methyl ether

Ethyl 3,3-diphenylpropanoate Structure

Ethyl 3,3-diphe...

~%

Benzenebutanoic acid, g-phenyl- Structure

Benzenebutanoic...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

1,4-Naphthalenedione,2-[3-(4-chlorophenyl)propyl]-3-hydroxy- Structure

1,4-Naphthalene...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

1,4-Naphthalenedione,2-[3-(4-chlorophenyl)propyl]-3-hydroxy- Structure

1,4-Naphthalene...

2-Hydroxy-1,4-naphoquinone Structure

2-Hydroxy-1,4-n...

~%

1,4-Naphthalenedione,2-[3-(4-chlorophenyl)propyl]-3-hydroxy- Structure

1,4-Naphthalene...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

4-hydroxy-3-undecylnaphthalene-1,2-dione Structure

4-hydroxy-3-und...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

4-hydroxy-3-undecylnaphthalene-1,2-dione Structure

4-hydroxy-3-und...

4-Phenylbutyric acid Structure

4-Phenylbutyric acid

~%

4-Cyclohexyl-1-butanol Structure

4-Cyclohexyl-1-...

Ethanol Structure

Cyclohexanebutyric acid Structure

Cyclohexanebuty...

~%

4-Cyclohexyl-1-butanol Structure

4-Cyclohexyl-1-...

butadiene Structure

TFIIH Modulator19 Structure

TFIIH Modulator19

~%

1,4-Naphthalenedione,2-phenyl- Structure

1,4-Naphthalene...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

1,4-Naphthalenedione,2,2'-methylenebis[3- hydroxy- Structure

1,4-Naphthalene...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

1,4-Naphthalenedione,2,2'-methylenebis[3- hydroxy- Structure

1,4-Naphthalene...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

1,4-Naphthalenedione,2-(3,7-dimethyloctyl)-3-hydroxy- Structure

1,4-Naphthalene...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

1,4-Naphthalenedione,2-(3,7-dimethyloctyl)-3-hydroxy- Structure

1,4-Naphthalene...

2-Hydroxy-1,4-naphoquinone Structure

2-Hydroxy-1,4-n...

~%

1,4-Naphthalenedione,2-(3,7-dimethyloctyl)-3-hydroxy- Structure

1,4-Naphthalene...

Calcium cyanamide Structure

Calcium cyanamide

~%

(3,4-dioxonaphthalen-1-yl)cyanamide Structure

(3,4-dioxonapht...

1,4-Naphthalenediol,1,4-diacetate Structure

1,4-Naphthalene...

~%

4-propan-2-yloxynaphthalen-1-ol Structure

4-propan-2-ylox...

(4-acetyloxy-5,8-dihydronaphthalen-1-yl) acetate Structure

(4-acetyloxy-5,...

~%

4-propan-2-yloxynaphthalen-1-ol Structure

4-propan-2-ylox...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

4-propan-2-yloxynaphthalen-1-ol Structure

4-propan-2-ylox...

2-Hydroxy-1,4-naphoquinone Structure

2-Hydroxy-1,4-n...

Isopropanol Structure

~%

2-propan-2-yloxynaphthalene-1,4-dione Structure

2-propan-2-ylox...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

2-propan-2-yloxynaphthalene-1,4-dione Structure

2-propan-2-ylox...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

2-propan-2-yloxynaphthalene-1,4-dione Structure

2-propan-2-ylox...

6-(4-chlorophenyl)-6-oxohexanoic acid Structure

6-(4-chlorophen...

~%

6-(4-chlorophenyl)hexanoic acid Structure

6-(4-chlorophen...

2-Hydroxy-1,4-naphoquinone Structure

2-Hydroxy-1,4-n...

~%

2-morpholin-4-ylnaphthalene-1,4-dione Structure

2-morpholin-4-y...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

2-morpholin-4-ylnaphthalene-1,4-dione Structure

2-morpholin-4-y...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

2-morpholin-4-ylnaphthalene-1,4-dione Structure

2-morpholin-4-y...

morpholine Structure

Lawsone methyl ether Structure

Lawsone methyl ether

~%

2-morpholin-4-ylnaphthalene-1,4-dione Structure

2-morpholin-4-y...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

1,4-Naphthalenedione, 2-hydroxy-3-(3-(4-phenoxyphenyl)propyl)- Structure

1,4-Naphthalene...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

1,4-Naphthalenedione, 2-hydroxy-3-(3-(4-phenoxyphenyl)propyl)- Structure

1,4-Naphthalene...

2-Hydroxy-1,4-naphoquinone Structure

2-Hydroxy-1,4-n...

~%

1,4-Naphthalenedione, 2-hydroxy-3-(3-(4-phenoxyphenyl)propyl)- Structure

1,4-Naphthalene...

Undecanoyl chloride Structure

Undecanoyl chloride

~%

3-decyl-4-hydroxy-naphthalene-1,2-dione Structure

3-decyl-4-hydro...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

(4-acetyloxy-5,8-dihydronaphthalen-1-yl) acetate Structure

(4-acetyloxy-5,...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

4-hydroxy-3-(2-methyloctyl)naphthalene-1,2-dione Structure

4-hydroxy-3-(2-...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

4-hydroxy-3-(2-methyloctyl)naphthalene-1,2-dione Structure

4-hydroxy-3-(2-...

2-Hydroxy-1,4-naphoquinone Structure

2-Hydroxy-1,4-n...

~%

4-hydroxy-3-(2-methyloctyl)naphthalene-1,2-dione Structure

4-hydroxy-3-(2-...

P-DIAZOBENZENESULFONIC ACID Structure

P-DIAZOBENZENES...

2-CYCLOHEXYLPHENOL Structure

2-CYCLOHEXYLPHENOL

~%

4-Amino-2-cyclohexylphenol Structure

4-Amino-2-cyclo...

N/A Structure

~%

5,9-dimethyldecanoic acid Structure

5,9-dimethyldec...

Decanoyl chloride Structure

Decanoyl chloride

~%

4-hydroxy-3-nonylnaphthalene-1,2-dione Structure

4-hydroxy-3-non...

ETHYLENE OXIDE Structure

~%

2-[3-(Trifluoromethyl)phenyl]ethanol Structure

2-[3-(Trifluoro...

Methanol Structure

~%

2-Naphthalenebutanoicacid, 5,6,7,8-tetrahydro-, methyl ester Structure

2-Naphthalenebu...

2-Hydroxy-1,4-naphoquinone Structure

2-Hydroxy-1,4-n...

ditridecanoyl peroxide Structure

ditridecanoyl p...

~%

2-Dodecyl-3-hydroxy-1,4-naphthoquinone Structure

2-Dodecyl-3-hyd...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

2-Dodecyl-3-hydroxy-1,4-naphthoquinone Structure

2-Dodecyl-3-hyd...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

2-Dodecyl-3-hydroxy-1,4-naphthoquinone Structure

2-Dodecyl-3-hyd...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

4-hydroxy-3-(4-methoxyphenyl)naphthalene-1,2-dione Structure

4-hydroxy-3-(4-...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

4-hydroxy-3-(4-methoxyphenyl)naphthalene-1,2-dione Structure

4-hydroxy-3-(4-...

2-Hydroxy-1,4-naphoquinone Structure

2-Hydroxy-1,4-n...

diheptanoyl peroxide Structure

diheptanoyl peroxide

~%

3-hexyl-4-hydroxynaphthalene-1,2-dione Structure

3-hexyl-4-hydro...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

3-hexyl-4-hydroxynaphthalene-1,2-dione Structure

3-hexyl-4-hydro...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

3-hexyl-4-hydroxynaphthalene-1,2-dione Structure

3-hexyl-4-hydro...

2-Hydroxy-1,4-naphoquinone Structure

2-Hydroxy-1,4-n...

Diisobutyryl peroxide Structure

Diisobutyryl pe...

~%

1,4-Naphthalenedione,2-hydroxy-3-(1-methylethyl)- Structure

1,4-Naphthalene...

1,2,4-Naphthalenetriol,1,2,4-triacetate Structure

1,2,4-Naphthale...

~%

1,4-Naphthalenedione,2-hydroxy-3-(1-methylethyl)- Structure

1,4-Naphthalene...

1,4-naphthoquinone Structure

1,4-naphthoquinone

~%

1,4-Naphthalenedione,2-hydroxy-3-(1-methylethyl)- Structure

1,4-Naphthalene...

(4-acetyloxy-5,8-dihydronaphthalen-1-yl) acetate Structure

(4-acetyloxy-5,...

~%

1,4-Naphthalenediol,1,4-diacetate Structure

1,4-Naphthalene...

Hexanoyl chloride TOP1 supplier Structure

Hexanoyl chlori...

~%

4-hydroxy-3-pentylnaphthalene-1,2-dione Structure

4-hydroxy-3-pen...