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 …

…, K Iwamoto, T HIGASHINO, AK MIYASHITA

Index: Suzuki, Yumiko; Takemura, Yuki; Iwamoto, Ken-Ichi; Higashino, Takeo; Miyashita, Akira Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 2 p. 199 - 206

Full Text: HTML

Citation Number: 22

Abstract

4-(α-Benzyl-α-hydroxybenzyl) quinazoline (4a) underwent retro-benzoin condensation catalyzed by cyanide ion to give deoxybenzoin (2a) and quinazoline (5a). Similarly, several nitrogen-containing heteroarenes (4, 9, 12, 16-19) having an α-hydroxybenzyl group at the α- position of the nitrogen underwent retro-benzoin type condensation to afford ketones (2) and heteroarenes (5). However, similar reaction of pyrazolopyrimidines (13, 14, 15) having an ...

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

phenyl-(3-pheny...

~%

3-phenyltriazolo[4,5-d]pyrimidine Structure

3-phenyltriazol...

Learn More

N/A Structure

~0%

2-Phenylacetophenone Structure

2-Phenylacetophenone

2-phenylquinoxaline Structure

2-phenylquinoxaline

Learn More

2,4-Dichloroquinazoline Structure

2,4-Dichloroqui...

~%

2-Methoxyquinazoline Structure

2-Methoxyquinazoline

Learn More

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

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

~%

2-Methoxyquinazoline Structure

2-Methoxyquinazoline

Learn More

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

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

~%

2-Methoxyquinazoline Structure

2-Methoxyquinazoline

Learn More

1-(4-methoxyphenyl)-1-(quinazolin-4-yl)ethanol Structure

1-(4-methoxyphe...

~72%

Quinazoline Structure

quinazoline-4-carboxylic acid amide Structure

quinazoline-4-c...

Acetanisole Structure

Learn More

N/A Structure

~69%

Acetanisole Structure

Learn More

N/A Structure

~84%

4-Methoxybenzophenone Structure

4-Methoxybenzop...

Learn More

N/A Structure

~0%

1-phenylphthalazine Structure

1-phenylphthalazine

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

1-(4-Methoxyphe...

Learn More

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

(4-methoxy-phen...

~%

4-benzyl-1-methylpyrazolo[3,4-d]pyrimidine Structure

4-benzyl-1-meth...

Learn More

N/A Structure

~8%

quinazoline-4-carbonitrile Structure

quinazoline-4-c...

quinazoline-4-carboxylic acid amide Structure

quinazoline-4-c...

N/A Structure

Detail Learn More

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

(4-methoxypheny...

~2%

4-Methoxybenzophenone Structure

4-Methoxybenzop...

quinazoline-4-carbonitrile Structure

quinazoline-4-c...

quinazoline-4-carboxylic acid amide Structure

quinazoline-4-c...

Learn More

POTASSIUM CYANIDE Structure

POTASSIUM CYANIDE

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

4-(α-benzyl-α-h...

~2%

2-Phenylacetophenone Structure

2-Phenylacetophenone

Quinazoline Structure

Detail Learn More

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

(4-methoxypheny...

~%

2-phenylquinazoline Structure

2-phenylquinazoline

Learn More

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...

Learn More

1-(4-methoxyphenyl)-1-(quinazolin-4-yl)ethanol Structure

1-(4-methoxyphe...

~0%

Quinazoline Structure

quinazoline-4-carboxylic acid amide Structure

quinazoline-4-c...

Acetanisole Structure

Learn More

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

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

~%

4-benzyl-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-benzyl-1-phen...

Learn More

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

(4-methoxy-phen...

~%

4-benzyl-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-benzyl-1-phen...

Learn More

N/A Structure

~83%

2-Phenylacetophenone Structure

2-Phenylacetophenone

2-phenylquinoxaline Structure

2-phenylquinoxaline

Learn More

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

phenyl-(3-pheny...

~%

2-phenylquinoxaline Structure

2-phenylquinoxaline

Learn More

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

(4-methoxypheny...

~%

2-phenylquinoxaline Structure

2-phenylquinoxaline

Learn More

N/A Structure

~67%

4-Methoxybenzophenone Structure

4-Methoxybenzop...

1-phenylphthalazine Structure

1-phenylphthalazine

Learn More

N/A Structure

~64%

1-phenylphthalazine Structure

1-phenylphthalazine

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

1-(4-Methoxyphe...

Learn More

N/A Structure

~35%

1-phenylphthalazine Structure

1-phenylphthalazine

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

1-(4-Methoxyphe...

Learn More

N/A Structure

~35%

1-phenylphthalazine Structure

1-phenylphthalazine

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

1-(4-Methoxyphe...

N/A Structure

Learn More

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

(4-methoxypheny...

~%

1-phenylphthalazine Structure

1-phenylphthalazine

Learn More

Triazolo [4, 5-d] pyrimidines. XI. Halogen-Metal Exchange Re...

[Tanji; Kato; Higashino Chemical and Pharmaceutical Bulletin, 1991 , vol. 39, # 11 p. 3037 - 3040]