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

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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 ...

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

89549-58-6

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

~84%

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

87412-75-7

4-(2-methoxyphe...

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

59563-85-8

(2-methoxypheny...

~%

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

87412-75-7

4-(2-methoxyphe...

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

89549-59-7

4-(p-methoxyphe...

~82%

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

87412-76-8

4-(4-methoxyphe...

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

89549-60-0

4-(2-chlorophen...

~72%

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

87412-78-0

4-(2-chlorophen...

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

5334-48-5

4-Chloro-1-phen...

~%

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

87412-78-0

4-(2-chlorophen...

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

89549-80-4

(2-chlorophenyl...

~2%

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

59563-88-1

(2-chloro-pheny...

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

87412-78-0

4-(2-chlorophen...

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

59563-88-1

(2-chloro-pheny...

~%

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

87412-78-0

4-(2-chlorophen...

2-Chlorobenzaldehyde Structure

89-98-5

2-Chlorobenzaldehyde

~%

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

87412-78-0

4-(2-chlorophen...

O-benzoyl-o-chloromandelonitrile Structure

89549-74-6

O-benzoyl-o-chl...

~%

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

87412-78-0

4-(2-chlorophen...

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

89549-80-4

(2-chlorophenyl...

~%

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

87412-78-0

4-(2-chlorophen...

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

89549-57-5

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

~82%

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

53645-78-6

1,4-diphenylpyr...

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

5334-48-5

4-Chloro-1-phen...

~%

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

53645-78-6

1,4-diphenylpyr...

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

89549-77-9

cyano(phenyl)(1...

~%

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

53645-78-6

1,4-diphenylpyr...

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

89549-61-1

4-(4-chlorophen...

~78%

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

87412-79-1

4-(4-chlorophen...

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

89549-81-5

(4-chlorophenyl...

~3%

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

87412-79-1

4-(4-chlorophen...

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

59563-90-5

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

α-(Benzoyloxy)-4-chlorobenzeneacetonitrile Structure

19788-56-8

α-(Benzoyloxy)-...

~%

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

87412-79-1

4-(4-chlorophen...

4-Chlorobenzaldehyde Structure

104-88-1

4-Chlorobenzaldehyde

~%

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

87412-79-1

4-(4-chlorophen...

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

59563-90-5

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

~%

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

87412-79-1

4-(4-chlorophen...

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

89549-83-7

cyano(4-fluorop...

~55%

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

89549-55-3

(4-fluorophenyl...

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

89549-66-6

4-(4-fluorophen...

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

5334-48-5

4-Chloro-1-phen...

~%

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

89549-55-3

(4-fluorophenyl...

4-Fluorobenzaldehyde Structure

459-57-4

4-Fluorobenzaldehyde

~%

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

89549-55-3

(4-fluorophenyl...

O-benzoyl-p-fluoromandelonitrile Structure

89549-76-8

O-benzoyl-p-flu...

~%

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

89549-55-3

(4-fluorophenyl...

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

89549-84-8

cyano(4-cyanoph...

~27%

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

89549-56-4

4-(1-phenylpyra...

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

55705-10-7

2-benzoyloxy-2(...

~%

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

89549-56-4

4-(1-phenylpyra...

4-Cyanobenzaldehyde Structure

105-07-7

4-Cyanobenzaldehyde

~%

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

89549-56-4

4-(1-phenylpyra...

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

5334-48-5

4-Chloro-1-phen...

~%

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

89549-56-4

4-(1-phenylpyra...

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

89549-62-2

4-(p-bromopheny...

~80%

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

89549-65-5

4-(4-bromopheny...

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

5334-48-5

4-Chloro-1-phen...

~%

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

89549-65-5

4-(4-bromopheny...

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

89549-82-6

(4-bromophenyl)...

~2%

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

89549-54-2

(4-bromophenyl)...

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

89549-65-5

4-(4-bromopheny...

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

89549-75-7

benzoic acid (4...

~%

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

89549-65-5

4-(4-bromopheny...

4-Bromobenzaldehyde Structure

1122-91-4

4-Bromobenzaldehyde

~%

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

89549-65-5

4-(4-bromopheny...

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

89549-82-6

(4-bromophenyl)...

~%

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

89549-65-5

4-(4-bromopheny...

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

89549-63-3

4-(4-fluorophen...

~79%

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

89549-66-6

4-(4-fluorophen...

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

5334-48-5

4-Chloro-1-phen...

~%

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

89549-66-6

4-(4-fluorophen...

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

89549-83-7

cyano(4-fluorop...

~2%

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

89549-55-3

(4-fluorophenyl...

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

89549-66-6

4-(4-fluorophen...

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

89549-55-3

(4-fluorophenyl...

~%

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

89549-66-6

4-(4-fluorophen...

4-Fluorobenzaldehyde Structure

459-57-4

4-Fluorobenzaldehyde

~%

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

89549-66-6

4-(4-fluorophen...

O-benzoyl-p-fluoromandelonitrile Structure

89549-76-8

O-benzoyl-p-flu...

~%

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

89549-66-6

4-(4-fluorophen...

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

89549-83-7

cyano(4-fluorop...

~%

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

89549-66-6

4-(4-fluorophen...

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

89549-77-9

cyano(phenyl)(1...

~62%

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

59563-84-7

phenyl-(1-pheny...

.alpha.-Cyanobenzyl benzoate Structure

4242-46-0

.alpha.-Cyanobe...

~%

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

59563-84-7

phenyl-(1-pheny...

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

89549-64-4

4-(4-cyanopheny...

~72%

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

89549-67-7

4-(1-phenylpyra...

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

5334-48-5

4-Chloro-1-phen...

~%

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

89549-67-7

4-(1-phenylpyra...

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

89549-56-4

4-(1-phenylpyra...

~%

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

89549-67-7

4-(1-phenylpyra...

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

89549-84-8

cyano(4-cyanoph...

~%

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

89549-67-7

4-(1-phenylpyra...

N/A Structure

89549-85-9

N/A

~19%

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

89549-86-0

4-(4-nitropheny...

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

69001-69-0

(4-nitrophenyl)...

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

5334-48-5

4-Chloro-1-phen...

~%

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

69001-69-0

(4-nitrophenyl)...

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

51130-02-0

[cyano-(4-nitro...

~%

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

69001-69-0

(4-nitrophenyl)...

4-Nitrobenzaldehyde Structure

555-16-8

4-Nitrobenzaldehyde

~%

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

69001-69-0

(4-nitrophenyl)...

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

53645-78-6

1,4-diphenylpyr...

~80%

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

76990-17-5

4-anilino-6-phe...

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

59563-84-7

phenyl-(1-pheny...

~%

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

76990-17-5

4-anilino-6-phe...

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

5334-48-5

4-Chloro-1-phen...

~%

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

76990-17-5

4-anilino-6-phe...

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

89549-57-5

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

~%

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

76990-17-5

4-anilino-6-phe...

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

89549-77-9

cyano(phenyl)(1...

~%

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

76990-17-5

4-anilino-6-phe...

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

87412-76-8

4-(4-methoxyphe...

~83%

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

89549-69-9

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

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

89549-59-7

4-(p-methoxyphe...

~%

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

89549-69-9

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

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

59563-87-0

(4-methoxy-phen...

~%

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

89549-69-9

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

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

89549-86-0

4-(4-nitropheny...

~84%

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

89549-70-2

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

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

69001-69-0

(4-nitrophenyl)...

~52%

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

89549-86-0

4-(4-nitropheny...

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

89549-70-2

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

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

5334-48-5

4-Chloro-1-phen...

~%

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

89549-70-2

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

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

51130-02-0

[cyano-(4-nitro...

~%

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

89549-70-2

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

4-Nitrobenzaldehyde Structure

555-16-8

4-Nitrobenzaldehyde

~%

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

89549-70-2

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

N/A Structure

89549-85-9

N/A

~%

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

89549-70-2

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

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

69001-69-0

(4-nitrophenyl)...

~%

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

89549-70-2

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

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

53645-73-1

4-methyl-1-phen...

~58%

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

89549-71-3

4-anilino-6-met...

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

69001-69-0

(4-nitrophenyl)...

~22%

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

89549-86-0

4-(4-nitropheny...

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

89549-70-2

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

N/A Structure

89549-85-9

N/A

~16%

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

89549-86-0

4-(4-nitropheny...

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

69001-69-0

(4-nitrophenyl)...

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

5334-48-5

4-Chloro-1-phen...

~%

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

89549-86-0

4-(4-nitropheny...

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

51130-02-0

[cyano-(4-nitro...

~%

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

89549-86-0

4-(4-nitropheny...

4-Nitrobenzaldehyde Structure

555-16-8

4-Nitrobenzaldehyde

~%

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

89549-86-0

4-(4-nitropheny...

N/A Structure

89549-85-9

N/A

~%

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

89549-86-0

4-(4-nitropheny...


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