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

Carbon-Carbon Bond Cleavage of. ALPHA.-Hydroxybenzylheteroarenes Catalyzed by Cyanide Ion: Retro-Benzoin Condensation Affords Ketones and Heteroarenes …

Y Suzuki, Y Takemura, K Iwamoto…

Index: Chemical and Pharmaceutical Bulletin, , vol. 46, # 2 p. 199 - 206

Full Text: HTML

Citation Number: 22

Abstract

... This reaction is considered to proceed through a retro-benzoin condensation mechanism.” As shown in Chart 1, the known analogy between the chemical behavior of ... O / / NAM] DMF NJ\Ph N)\Ph 9c (Ar: o) 2c (Ar = C) 5b 8b 5% Chart 2 © 1998 Pharmaceutical Society of ... 200 Vol. ...

4-(α-benzyl-α-hydroxybenzyl)quinazoline Structure

4-(α-benzyl-α-h...

~91%

2-Phenylacetophenone Structure

2-Phenylacetophenone

Quinazoline Structure

N/A Structure

~66%

quinazoline-4-carbonitrile Structure

quinazoline-4-c...

quinazoline-4-carboxylic acid amide Structure

quinazoline-4-c...

N/A Structure

Detail

(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-o-tolyl-methanone Structure

(1-phenyl-1H-py...

~%

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

1-(1-methyl-1H-benzo[d]imidazol-2-yl)-1,2-diphenylethanol Structure

1-(1-methyl-1H-...

~67%

2-Phenylacetophenone Structure

2-Phenylacetophenone

1-Methylbenzimidazole Structure

1-Methylbenzimi...

Benzyl magnesium bromide Structure

Benzyl magnesiu...

~%

2-Phenylacetophenone Structure

2-Phenylacetophenone

POTASSIUM CYANIDE Structure

POTASSIUM CYANIDE

4-(α-benzyl-α-hydroxybenzyl)quinazoline Structure

4-(α-benzyl-α-h...

~70%

2-Phenylacetophenone Structure

2-Phenylacetophenone

Quinazoline Structure

Detail

N/A Structure

~%

2-phenylquinazoline Structure

2-phenylquinazoline

1-(4-Methoxyphenyl)-2-phenylethanone Structure

1-(4-Methoxyphe...

2-phenyl-4-benzylquinazoline Structure

2-phenyl-4-benz...

phenyl(quinazolin-4-yl)methanone Structure

phenyl(quinazol...

~%

2-Phenylacetophenone Structure

2-Phenylacetophenone

Methanone,2-benzothiazolylphenyl- Structure

Methanone,2-ben...

~%

2-Phenylacetophenone Structure

2-Phenylacetophenone

phenyl-(3-phenylquinoxalin-2-yl)methanone Structure

phenyl-(3-pheny...

~%

2-Phenylacetophenone Structure

2-Phenylacetophenone

phenyl-(3-phenyltriazolo[4,5-d]pyrimidin-7-yl)methanone Structure

phenyl-(3-pheny...

~%

2-Phenylacetophenone Structure

2-Phenylacetophenone

(1-methyl-1H-benzoimidazol-2-yl)-phenyl-methanone Structure

(1-methyl-1H-be...

~%

2-Phenylacetophenone Structure

2-Phenylacetophenone

N/A Structure

~%

Acetanisole Structure

(4-methoxyphenyl)-quinazolin-4-ylmethanone Structure

(4-methoxypheny...

~%

Acetanisole Structure

N/A Structure

~91%

4-Methoxybenzophenone Structure

4-Methoxybenzop...

1-phenylphthalazine Structure

1-phenylphthalazine

(4-methoxyphenyl)(phenyl)(quinazolin-4-yl)methanol Structure

(4-methoxypheny...

~64%

4-Methoxybenzophenone Structure

4-Methoxybenzop...

quinazoline-4-carbonitrile Structure

quinazoline-4-c...

quinazoline-4-carboxylic acid amide Structure

quinazoline-4-c...

N/A Structure

~76%

Quinazoline Structure

1-(4-Methoxyphenyl)-2-phenylethanone Structure

1-(4-Methoxyphe...

quinazoline-4-carboxylic acid amide Structure

quinazoline-4-c...

N/A Structure

~39%

1-phenylphthalazine Structure

1-phenylphthalazine

1-(4-Methoxyphenyl)-2-phenylethanone Structure

1-(4-Methoxyphe...

N/A Structure

~39%

1-phenylphthalazine Structure

1-phenylphthalazine

1-(4-Methoxyphenyl)-2-phenylethanone Structure

1-(4-Methoxyphe...

N/A Structure

Benzyl magnesium bromide Structure

Benzyl magnesiu...

~%

1-(4-Methoxyphenyl)-2-phenylethanone Structure

1-(4-Methoxyphe...

(4-methoxyphenyl)(2-phenylquinazolin-4-yl)methanone Structure

(4-methoxypheny...

~%

1-(4-Methoxyphenyl)-2-phenylethanone Structure

1-(4-Methoxyphe...

(4-methoxyphenyl)(4-phenylphthalazin-1-yl)methanone Structure

(4-methoxypheny...

~%

1-(4-Methoxyphenyl)-2-phenylethanone Structure

1-(4-Methoxyphe...

(4-methoxyphenyl)(3-phenylquinoxalin-2-yl)methanone Structure

(4-methoxypheny...

~%

1-(4-Methoxyphenyl)-2-phenylethanone Structure

1-(4-Methoxyphe...

4-(α-methyl-α-hydroxy-p-bromobenzyl)-2-chloroquinazoline Structure

4-(α-methyl-α-h...

~91%

2-Chloroquinazoline Structure

2-Chloroquinazoline

1-(4-Bromophenyl)ethanone Structure

1-(4-Bromopheny...

4-(α-methyl-α-hydroxy-p-bromobenzyl)-2-dimethylaminoquinazoline Structure

4-(α-methyl-α-h...

~55%

1-(4-Bromophenyl)ethanone Structure

1-(4-Bromopheny...

dimethyl-quinazolin-2-yl-amine Structure

dimethyl-quinaz...

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

~%

1-(4-Bromophenyl)ethanone Structure

1-(4-Bromopheny...

2-chloro-4-(p-bromobenzoyl)quinazoline Structure

2-chloro-4-(p-b...

~%

1-(4-Bromophenyl)ethanone Structure

1-(4-Bromopheny...

2-methoxy-4-(p-bromobenzoyl)quinazoline Structure

2-methoxy-4-(p-...

~%

1-(4-Bromophenyl)ethanone Structure

1-(4-Bromopheny...

4-(p-bromobenzoyl)-2-dimethylaminoquinazoline Structure

4-(p-bromobenzo...

~%

1-(4-Bromophenyl)ethanone Structure

1-(4-Bromopheny...

phenylmagnesium bromide Structure

phenylmagnesium...

~%

4-Methoxybenzophenone Structure

4-Methoxybenzop...

Iodo(phenyl)magnesium Structure

Iodo(phenyl)mag...

~%

4-Methoxybenzophenone Structure

4-Methoxybenzop...

N/A Structure

~%

4-Methoxybenzophenone Structure

4-Methoxybenzop...

(4-methoxyphenyl)(4-phenylphthalazin-1-yl)methanone Structure

(4-methoxypheny...

~%

4-Methoxybenzophenone Structure

4-Methoxybenzop...

4-(α-methyl-α-hydroxy-p-bromobenzyl)-2-chloroquinazoline Structure

4-(α-methyl-α-h...

~38%

2-Chloroquinazoline Structure

2-Chloroquinazoline

1-(4-Bromophenyl)ethanone Structure

1-(4-Bromopheny...

2-chloro-4-(p-bromobenzoyl)quinazoline Structure

2-chloro-4-(p-b...

~%

2-Chloroquinazoline Structure

2-Chloroquinazoline

4-(α-benzyl-α-hydroxybenzyl)quinazoline Structure

4-(α-benzyl-α-h...

~87%

2-Phenylacetophenone Structure

2-Phenylacetophenone

Quinazoline Structure

N/A Structure

~15%

Quinazoline Structure

1-(2-furyl)-2-phenylethanone Structure

1-(2-furyl)-2-p...

quinazoline-4-carboxylic acid amide Structure

quinazoline-4-c...

Detail

N/A Structure

~6%

Quinazoline Structure

1-(4-Methoxyphenyl)-2-phenylethanone Structure

1-(4-Methoxyphe...

quinazoline-4-carboxylic acid amide Structure

quinazoline-4-c...

POTASSIUM CYANIDE Structure

POTASSIUM CYANIDE

4-(α-benzyl-α-hydroxybenzyl)quinazoline Structure

4-(α-benzyl-α-h...

~33%

2-Phenylacetophenone Structure

2-Phenylacetophenone

Quinazoline Structure

Detail

phenyl(quinazolin-4-yl)methanone Structure

phenyl(quinazol...

~%

Quinazoline Structure

(4-methoxyphenyl)-quinazolin-4-ylmethanone Structure

(4-methoxypheny...

~%

Quinazoline Structure

Benzyl magnesium bromide Structure

Benzyl magnesiu...

~%

Quinazoline Structure

1-(1-methyl-1H-benzo[d]imidazol-2-yl)-1,2-diphenylethanol Structure

1-(1-methyl-1H-...

~36%

2-Phenylacetophenone Structure

2-Phenylacetophenone

1-Methylbenzimidazole Structure

1-Methylbenzimi...

(1-methyl-1H-benzoimidazol-2-yl)-phenyl-methanone Structure

(1-methyl-1H-be...

~%

1-Methylbenzimidazole Structure

1-Methylbenzimi...

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