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

One-pot oxidation of azomethine compounds into arenecarboxylic acids

…, SB Said, L Syper, J Młochowski

Index: Giurg; Said; Syper; Mlochowski Synthetic Communications, 2001 , vol. 31, # 20 p. 3151 - 3159

Full Text: HTML

Citation Number: 24

Abstract

Aromatic azomethine compounds, such as aldazines 1, aldoximes 7 and tosylhydrazones 8 oxidized with 30% hydrogen peroxide in the presence of poly (bis-1, 2-phenylene) diselenide (6) as catalyst produce arenecarboxylic acids 2 mostly in high to excellent yields. The presented one-pot procedure has a synthetic value.

2-methoxybenzaldehyde p-toluenesulfonylhydrazone Structure

2-methoxybenzal...

~40%

2-Methoxybenzoic acid Structure

2-Methoxybenzoi...

2-Methoxybenzalazine Structure

2-Methoxybenzalazine

~18%

2-Methoxybenzoic acid Structure

2-Methoxybenzoi...

o-Anisaldehyde Oxime Structure

o-Anisaldehyde Oxime

~15%

2-Methoxybenzoic acid Structure

2-Methoxybenzoi...

2,6-Dichlorobenzaldoxime Structure

2,6-Dichloroben...

~93%

2,6-Dichlorobenzoic acid Structure

2,6-Dichloroben...

N'-(2,6-dichlorobenzylidene)-4-methylbenzene-1-sulfonohydrazide Structure

N'-(2,6-dichlor...

~94%

2,6-Dichlorobenzoic acid Structure

2,6-Dichloroben...

3-phenoxybenzaldehyde oxime Structure

3-phenoxybenzal...

~93%

3-Phenoxybenzoic acid Structure

3-Phenoxybenzoi...

3,4,5-trimethoxybenzaldehyde p-toluenesulphonylhydrazone Structure

3,4,5-trimethox...

~68%

Trimethylgallic acid Structure

Trimethylgallic acid

1-(3,4,5-trimethoxyphenyl)-N-[(3,4,5-trimethoxyphenyl)methylideneamino]methanimine Structure

1-(3,4,5-trimet...

~32%

Trimethylgallic acid Structure

Trimethylgallic acid

3,4,5-TRIMETHOXYBENZALDOXIME Structure

3,4,5-TRIMETHOX...

~16%

Trimethylgallic acid Structure

Trimethylgallic acid

3-nitrobenzaldehyde N-[-(3-nitrophenyl)methylidene]hydrazone Structure

3-nitrobenzalde...

~99%

3-Nitrobenzoic acid Structure

3-Nitrobenzoic acid

Benzaldehyde, 3-nitro-,oxime Structure

Benzaldehyde, 3...

~94%

3-Nitrobenzoic acid Structure

3-Nitrobenzoic acid

Benzenesulfonic acid,4-methyl-, 2-[(3-nitrophenyl)methylene]hydrazide Structure

Benzenesulfonic...

~10%

3-Nitrobenzoic acid Structure

3-Nitrobenzoic acid

1-Naphthalenecarboxaldehyde,oxime Structure

1-Naphthaleneca...

~30%

Phthalide-3-Acetic Acid Structure

Phthalide-3-Ace...

naphthoic acid Structure

1-Naphthalenecarboxaldehyde,2-(1-naphthalenylmethylene)hydrazone Structure

1-Naphthaleneca...

~24%

Phthalide-3-Acetic Acid Structure

Phthalide-3-Ace...

naphthoic acid Structure

N/A Structure

~15%

Phthalide-3-Acetic Acid Structure

Phthalide-3-Ace...

naphthoic acid Structure

4-(HYDROXYIMINO-METHYL)-BENZOIC ACID METHYL ESTER Structure

4-(HYDROXYIMINO...

~93%

mono-methyl_terephthalate Structure

mono-methyl_ter...

N/A Structure

~98%

mono-methyl_terephthalate Structure

mono-methyl_ter...

dimethyl 4,4'-(hydrazine-1,2-diylidenebis(methanylylidene))dibenzoate Structure

dimethyl 4,4'-(...

~93%

mono-methyl_terephthalate Structure

mono-methyl_ter...

p-Fluorobenzaldehyde oxime Structure

p-Fluorobenzald...

~99%

4-Fluorobenzoic acid Structure

4-Fluorobenzoic acid

N'-(4-fluorobenzylidene)-4-methylbenzenesulfonohydrazide Structure

N'-(4-fluoroben...

~95%

4-Fluorobenzoic acid Structure

4-Fluorobenzoic acid

p-fluorobenzaldazine Structure

p-fluorobenzaldazine

~92%

4-Fluorobenzoic acid Structure

4-Fluorobenzoic acid

1-Naphthalenecarboxaldehyde,oxime Structure

1-Naphthaleneca...

~0%

Phthalide-3-Acetic Acid Structure

Phthalide-3-Ace...

naphthoic acid Structure

1-Naphthalenecarboxaldehyde,2-(1-naphthalenylmethylene)hydrazone Structure

1-Naphthaleneca...

~0%

Phthalide-3-Acetic Acid Structure

Phthalide-3-Ace...

naphthoic acid Structure

N/A Structure

~0%

Phthalide-3-Acetic Acid Structure

Phthalide-3-Ace...

naphthoic acid Structure

1-Naphthalenol Structure

~26%

Phthalide-3-Acetic Acid Structure

Phthalide-3-Ace...

DMeOB Structure

~92%

3-Methoxybenzoic acid Structure

3-Methoxybenzoi...

3-methoxybenzaldoxime Structure

3-methoxybenzal...

~96%

3-Methoxybenzoic acid Structure

3-Methoxybenzoi...

N'-(3-methoxybenzylidene)-4-methylbenzen sulfonohydrazide Structure

N'-(3-methoxybe...

~98%

3-Methoxybenzoic acid Structure

3-Methoxybenzoi...

4-Isopropylbenzaldehyde Structure

4-Isopropylbenz...

~%

Benzaldehyde,4-(1-methylethyl)-, 2-[[4-(1-methylethyl)phenyl]methylene]hydrazone Structure

Benzaldehyde,4-...

2-CHLORO-6-FLUOROBENZALDOXIME Structure

2-CHLORO-6-FLUO...

~99%

2-Chloro-6-fluorobenzoic acid Structure

2-Chloro-6-fluo...

N-[(4-methoxyphenyl)methylideneamino]-4-methyl-benzenesulfonamide Structure

N-[(4-methoxyph...

~39%

p-Anisic acid Structure

4-methoxybenzaldehyde azine Structure

4-methoxybenzal...

~24%

p-Anisic acid Structure

Benzaldehyde,4-methoxy-, oxime, (E)- Structure

Benzaldehyde,4-...

~23%

p-Anisic acid Structure

Benzaldehyde,4-methyl-, oxime Structure

Benzaldehyde,4-...

~99%

4-Methylbenzoic acid Structure

4-Methylbenzoic acid

4-methyl-N'-[(1E)-(4-methylphenyl)methylidene]benzene-1-sulfonohydrazide Structure

4-methyl-N'-[(1...

~98%

4-Methylbenzoic acid Structure

4-Methylbenzoic acid

1-(4-methylphenyl)-N-[(4-methylphenyl)methylideneamino]methanimine Structure

1-(4-methylphen...

~99%

4-Methylbenzoic acid Structure

4-Methylbenzoic acid

(E)-2-Naphthalenecarbaldehyde oxime Structure

(E)-2-Naphthale...

~97%

2-Naphthoic acid Structure

2-Naphthoic acid

2-napthaldehyde N-[-(2-napthyl)methylidene]hydrazone Structure

2-napthaldehyde...

~97%

2-Naphthoic acid Structure

2-Naphthoic acid

1-(2,4-dichlorophenyl)-N-[(2,4-dichlorophenyl)methylideneamino]methanimine Structure

1-(2,4-dichloro...

~99%

2,4-Dichlorobenzoic acid Structure

2,4-Dichloroben...

Benzaldehyde,2,4-dichloro-, oxime Structure

Benzaldehyde,2,...

~98%

2,4-Dichlorobenzoic acid Structure

2,4-Dichloroben...

2,4-Dichlor-1-(p-toluol-sulfonyl-hydrazino-methyl)-benzol Structure

2,4-Dichlor-1-(...

~99%

2,4-Dichlorobenzoic acid Structure

2,4-Dichloroben...

Benzenesulfonic acid,4-methyl-, 2-[(4-nitrophenyl)methylene]hydrazide Structure

Benzenesulfonic...

~91%

4-Nitrobenzoic acid Structure

4-Nitrobenzoic acid

o-chlorobenzaldoxime Structure

o-chlorobenzaldoxime

~89%

2-Chlorobenzoic acid Structure

2-Chlorobenzoic acid

Benzaldehyde,2-chloro-, 2-[(2-chlorophenyl)methylene]hydrazone Structure

Benzaldehyde,2-...

~98%

2-Chlorobenzoic acid Structure

2-Chlorobenzoic acid

2-chlorobenzaldehyde tosylhydrazone Structure

2-chlorobenzald...

~98%

2-Chlorobenzoic acid Structure

2-Chlorobenzoic acid

Beyond aresta's complex: Ni-and Pd-catalyzed organozinc coup...

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Rhodium (I)-catalyzed carboxylation of aryl-and alkenylboron...

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A New Indirect Application of Aggregative Activation: Synthe...

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Phase-vanishing methodology for efficient bromination, alkyl...

[Jana, Nirmal K.; Verkade, John G. Organic Letters, 2003 , vol. 5, # 21 p. 3787 - 3790]

Directed ortho??Metalation, a New Insight into Organosodium ...

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