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

Studies on pyrazolo (3, 4-d) pyrimidine derivatives. XIII. Aryl migration of 4-aroyl-1H-pyrazolo (3, 4-d) pyrimidines to 4-aryl-4, 5-dihydro-1H-pyrazolo (3, 4-d) pyrimidine …

東野武郎，松下保彦，竹元万寿美，林英作

Index: Higashino, Takeo; Matsushita, Yasuhiko; Takemoto, Masumi; Hayashi, Eisaku Chemical and Pharmaceutical Bulletin, 1983 , vol. 31, # 11 p. 3951 - 3958

Full Text: HTML

Citation Number: 0

Abstract

... 4,5-dihydro-1H-pyrazolol3,4-d]pyrimidine—4— carboxylic Acids TAKEo HIGASHINO,* YASUHIKO MATSUSHITA, MASUMI TAKEMOTO, and EISAKU HAYASHI Shizuoka College ... benzilic acid rearrangement; ring ﬁssion It has been reported that the chemical properties of ...

4,5-dihydro-4-(2-methoxyphenyl)-1-phenyl-1H-pyrazolo(3.4-d)pyrimidine-4-carboxylic acid Structure

4,5-dihydro-4-(...

~84%

4-(2-methoxyphenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(2-methoxyphe...

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

(2-methoxypheny...

~%

4-(2-methoxyphenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(2-methoxyphe...

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4-(p-methoxyphenyl)-4,5-dihydro-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4-carboxylic acid Structure

4-(p-methoxyphe...

~82%

4-(4-methoxyphenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-methoxyphe...

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4-(2-chlorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-4-carboxylic acid Structure

4-(2-chlorophen...

~72%

4-(2-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(2-chlorophen...

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4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine Structure

4-Chloro-1-phen...

~%

4-(2-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(2-chlorophen...

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(2-chlorophenyl)(cyano)(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)methyl benzoate Structure

(2-chlorophenyl...

~2%

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

(2-chloro-pheny...

4-(2-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(2-chlorophen...

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

(2-chloro-pheny...

~%

4-(2-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(2-chlorophen...

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2-Chlorobenzaldehyde Structure

2-Chlorobenzaldehyde

~%

4-(2-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(2-chlorophen...

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O-benzoyl-o-chloromandelonitrile Structure

O-benzoyl-o-chl...

~%

4-(2-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(2-chlorophen...

Learn More

(2-chlorophenyl)(cyano)(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)methyl benzoate Structure

(2-chlorophenyl...

~%

4-(2-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(2-chlorophen...

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4-phenyl-4,5-dihydro-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4-carboxylic acid Structure

4-phenyl-4,5-di...

~82%

1,4-diphenylpyrazolo[3,4-d]pyrimidine Structure

1,4-diphenylpyr...

Learn More

4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine Structure

4-Chloro-1-phen...

~%

1,4-diphenylpyrazolo[3,4-d]pyrimidine Structure

1,4-diphenylpyr...

Learn More

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

cyano(phenyl)(1...

~%

1,4-diphenylpyrazolo[3,4-d]pyrimidine Structure

1,4-diphenylpyr...

Learn More

4-(4-chlorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-4-carboxylic acid Structure

4-(4-chlorophen...

~78%

4-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-chlorophen...

Learn More

(4-chlorophenyl)(cyano)(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)methyl benzoate Structure

(4-chlorophenyl...

~3%

4-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-chlorophen...

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

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

Learn More

α-(Benzoyloxy)-4-chlorobenzeneacetonitrile Structure

α-(Benzoyloxy)-...

~%

4-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-chlorophen...

Learn More

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

~%

4-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-chlorophen...

Learn More

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

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

~%

4-(4-chlorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-chlorophen...

Learn More

cyano(4-fluorophenyl)(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)methyl benzoate Structure

cyano(4-fluorop...

~55%

(4-fluorophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-fluorophenyl...

4-(4-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-fluorophen...

Learn More

4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine Structure

4-Chloro-1-phen...

~%

(4-fluorophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-fluorophenyl...

Learn More

4-Fluorobenzaldehyde Structure

4-Fluorobenzaldehyde

~%

(4-fluorophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-fluorophenyl...

Learn More

O-benzoyl-p-fluoromandelonitrile Structure

O-benzoyl-p-flu...

~%

(4-fluorophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-fluorophenyl...

Learn More

cyano(4-cyanophenyl)(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)methyl benzoate Structure

cyano(4-cyanoph...

~27%

4-(1-phenylpyrazolo[3,4-d]pyrimidine-4-carbonyl)benzonitrile Structure

4-(1-phenylpyra...

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2-benzoyloxy-2(4-cyanophenyl)acetonitrile Structure

2-benzoyloxy-2(...

~%

4-(1-phenylpyrazolo[3,4-d]pyrimidine-4-carbonyl)benzonitrile Structure

4-(1-phenylpyra...

Learn More

4-Cyanobenzaldehyde Structure

4-Cyanobenzaldehyde

~%

4-(1-phenylpyrazolo[3,4-d]pyrimidine-4-carbonyl)benzonitrile Structure

4-(1-phenylpyra...

Learn More

4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine Structure

4-Chloro-1-phen...

~%

4-(1-phenylpyrazolo[3,4-d]pyrimidine-4-carbonyl)benzonitrile Structure

4-(1-phenylpyra...

Learn More

4-(p-bromophenyl)-4,5-dihydro-1-phenyl-1H-pyrazolo(3,4-d)pyrimidine-4-carboxylic acid Structure

4-(p-bromopheny...

~80%

4-(4-bromophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-bromopheny...

Learn More

4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine Structure

4-Chloro-1-phen...

~%

4-(4-bromophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-bromopheny...

Learn More

(4-bromophenyl)(cyano)(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)methyl benzoate Structure

(4-bromophenyl)...

~2%

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

(4-bromophenyl)...

4-(4-bromophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-bromopheny...

Learn More

benzoic acid (4-bromophenyl)-cyano-methyl ester Structure

benzoic acid (4...

~%

4-(4-bromophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-bromopheny...

Learn More

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

~%

4-(4-bromophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-bromopheny...

Learn More

(4-bromophenyl)(cyano)(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)methyl benzoate Structure

(4-bromophenyl)...

~%

4-(4-bromophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-bromopheny...

Learn More

4-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-4-carboxylic acid Structure

4-(4-fluorophen...

~79%

4-(4-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-fluorophen...

Learn More

4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine Structure

4-Chloro-1-phen...

~%

4-(4-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-fluorophen...

Learn More

cyano(4-fluorophenyl)(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)methyl benzoate Structure

cyano(4-fluorop...

~2%

(4-fluorophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-fluorophenyl...

4-(4-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-fluorophen...

Learn More

(4-fluorophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-fluorophenyl...

~%

4-(4-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-fluorophen...

Learn More

4-Fluorobenzaldehyde Structure

4-Fluorobenzaldehyde

~%

4-(4-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-fluorophen...

Learn More

O-benzoyl-p-fluoromandelonitrile Structure

O-benzoyl-p-flu...

~%

4-(4-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-fluorophen...

Learn More

cyano(4-fluorophenyl)(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)methyl benzoate Structure

cyano(4-fluorop...

~%

4-(4-fluorophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-fluorophen...

Learn More

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

cyano(phenyl)(1...

~62%

phenyl-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

phenyl-(1-pheny...

Learn More

.alpha.-Cyanobenzyl benzoate Structure

.alpha.-Cyanobe...

~%

phenyl-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

phenyl-(1-pheny...

Learn More

4-(4-cyanophenyl)-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-4-carboxylic acid Structure

4-(4-cyanopheny...

~72%

4-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)benzonitrile Structure

4-(1-phenylpyra...

Learn More

4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine Structure

4-Chloro-1-phen...

~%

4-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)benzonitrile Structure

4-(1-phenylpyra...

Learn More

4-(1-phenylpyrazolo[3,4-d]pyrimidine-4-carbonyl)benzonitrile Structure

4-(1-phenylpyra...

~%

4-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)benzonitrile Structure

4-(1-phenylpyra...

Learn More

cyano(4-cyanophenyl)(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)methyl benzoate Structure

cyano(4-cyanoph...

~%

4-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)benzonitrile Structure

4-(1-phenylpyra...

Learn More

N/A Structure

~19%

4-(4-nitrophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-nitropheny...

(4-nitrophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-nitrophenyl)...

Learn More

4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine Structure

4-Chloro-1-phen...

~%

(4-nitrophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-nitrophenyl)...

Learn More

[cyano-(4-nitrophenyl)methyl] benzoate Structure

[cyano-(4-nitro...

~%

(4-nitrophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-nitrophenyl)...

Learn More

4-Nitrobenzaldehyde Structure

4-Nitrobenzaldehyde

~%

(4-nitrophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-nitrophenyl)...

Learn More

1,4-diphenylpyrazolo[3,4-d]pyrimidine Structure

1,4-diphenylpyr...

~80%

4-anilino-6-phenylpyrimidine-5-carbonitrile Structure

4-anilino-6-phe...

Learn More

phenyl-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

phenyl-(1-pheny...

~%

4-anilino-6-phenylpyrimidine-5-carbonitrile Structure

4-anilino-6-phe...

Learn More

4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine Structure

4-Chloro-1-phen...

~%

4-anilino-6-phenylpyrimidine-5-carbonitrile Structure

4-anilino-6-phe...

Learn More

4-phenyl-4,5-dihydro-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4-carboxylic acid Structure

4-phenyl-4,5-di...

~%

4-anilino-6-phenylpyrimidine-5-carbonitrile Structure

4-anilino-6-phe...

Learn More

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

cyano(phenyl)(1...

~%

4-anilino-6-phenylpyrimidine-5-carbonitrile Structure

4-anilino-6-phe...

Learn More

4-(4-methoxyphenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-methoxyphe...

~83%

4-anilino-6-(4-methoxyphenyl)pyrimidine-5-carbonitrile Structure

4-anilino-6-(4-...

Learn More

4-(p-methoxyphenyl)-4,5-dihydro-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4-carboxylic acid Structure

4-(p-methoxyphe...

~%

4-anilino-6-(4-methoxyphenyl)pyrimidine-5-carbonitrile Structure

4-anilino-6-(4-...

Learn More

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

(4-methoxy-phen...

~%

4-anilino-6-(4-methoxyphenyl)pyrimidine-5-carbonitrile Structure

4-anilino-6-(4-...

Learn More

4-(4-nitrophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-nitropheny...

~84%

4-anilino-6-(4-nitrophenyl)pyrimidine-5-carbonitrile Structure

4-anilino-6-(4-...

Learn More

(4-nitrophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-nitrophenyl)...

~52%

4-(4-nitrophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-nitropheny...

4-anilino-6-(4-nitrophenyl)pyrimidine-5-carbonitrile Structure

4-anilino-6-(4-...

Learn More

4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine Structure

4-Chloro-1-phen...

~%

4-anilino-6-(4-nitrophenyl)pyrimidine-5-carbonitrile Structure

4-anilino-6-(4-...

Learn More

[cyano-(4-nitrophenyl)methyl] benzoate Structure

[cyano-(4-nitro...

~%

4-anilino-6-(4-nitrophenyl)pyrimidine-5-carbonitrile Structure

4-anilino-6-(4-...

Learn More

4-Nitrobenzaldehyde Structure

4-Nitrobenzaldehyde

~%

4-anilino-6-(4-nitrophenyl)pyrimidine-5-carbonitrile Structure

4-anilino-6-(4-...

Learn More

N/A Structure

~%

4-anilino-6-(4-nitrophenyl)pyrimidine-5-carbonitrile Structure

4-anilino-6-(4-...

Learn More

(4-nitrophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-nitrophenyl)...

~%

4-anilino-6-(4-nitrophenyl)pyrimidine-5-carbonitrile Structure

4-anilino-6-(4-...

Learn More

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

4-methyl-1-phen...

~58%

4-anilino-6-methylpyrimidine-5-carbonitrile Structure

4-anilino-6-met...

Learn More

(4-nitrophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-nitrophenyl)...

~22%

4-(4-nitrophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-nitropheny...

4-anilino-6-(4-nitrophenyl)pyrimidine-5-carbonitrile Structure

4-anilino-6-(4-...

Learn More

N/A Structure

~16%

4-(4-nitrophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-nitropheny...

(4-nitrophenyl)-(1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)methanone Structure

(4-nitrophenyl)...

Learn More

4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine Structure

4-Chloro-1-phen...

~%

4-(4-nitrophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-nitropheny...

Learn More

[cyano-(4-nitrophenyl)methyl] benzoate Structure

[cyano-(4-nitro...

~%

4-(4-nitrophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-nitropheny...

Learn More

4-Nitrobenzaldehyde Structure

4-Nitrobenzaldehyde

~%

4-(4-nitrophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-nitropheny...

Learn More

N/A Structure

~%

4-(4-nitrophenyl)-1-phenylpyrazolo[3,4-d]pyrimidine Structure

4-(4-nitropheny...

Learn More

Aryl coupling reactions of pyrazolo [3, 4-d] pyrimidin-4-yl ...

[Press, Jeffery B.; Eudy, Nancy H.; Morton, George O. Journal of Organic Chemistry, 1983 , vol. 48, # 24 p. 4605 - 4611]