Studies on v-triazoles. 9. Antiallergic 4, 9-dihydro-4, 9-dioxo-1H-naphtho [2, 3-d]-v-triazoles

DR Buckle, H Smith, BA Spicer…

Index: Buckle; Smith; Spicer; Tedder Journal of Medicinal Chemistry, 1983 , vol. 26, # 5 p. 714 - 719

Full Text: HTML

Citation Number: 10

Abstract

12, R,(R,)= Me; 14, R,= R,= H 15, R,= Me; R,= H 16, R,= R,= Me Rz (Ri)= H 13, R,= R,= Me choice being largely dependent on the position and type of substitution. The parent compound, 14, was prepared from 2, 3-dichloronaphthoquinone by the method of Fieser and Martin: and an analogous procedure was used for the 6-methyl and 6, 7-dimethyl homologues, 15 and 16, respectively. Thus, bromination of the naphthoquinones 4 and 5 ( ...

 Related Synthetic Route
5-methylsulfanyl-2H-benzo[f]benzotriazole-4,9-dione Structure

84731-21-5

5-methylsulfany...

~77%

5-methylsulfinyl-2H-benzo[f]benzotriazole-4,9-dione Structure

84731-24-8

5-methylsulfiny...

5-methylsulfanyl-2H-benzo[f]benzotriazole-4,9-dione Structure

84731-21-5

5-methylsulfany...

~59%

5-methylsulfonyl-2H-benzo[f]benzotriazole-4,9-dione Structure

84731-25-9

5-methylsulfony...

1-[(4-methoxyphenyl)methyl]-1H,4H,9H-naphtho[2,3-d][1,2,3]triazole-4,9-dione Structure

79707-02-1

1-[(4-methoxyph...

~90%

2H-benzo[f]benzotriazole-4,9-dione Structure

3915-98-8

2H-benzo[f]benz...

1,4-naphthoquinone Structure

130-15-4

1,4-naphthoquinone

~%

2H-benzo[f]benzotriazole-4,9-dione Structure

3915-98-8

2H-benzo[f]benz...

N-(3-amino-1,4-dihydroxynaphthalen-2-yl)acetamide Structure

72365-04-9

N-(3-amino-1,4-...

~%

2H-benzo[f]benzotriazole-4,9-dione Structure

3915-98-8

2H-benzo[f]benz...

1,4-Naphthalenedione,6,7-dimethyl- Structure

2202-79-1

1,4-Naphthalene...

~76%

2,3-dibromo-6,7-dimethyl-naphthalene-1,4-dione Structure

41791-77-9

2,3-dibromo-6,7...

Ethanoic anhydride Structure

108-24-7

Ethanoic anhydride

3-amino-2-bromo-6,7-dimethyl-naphthalene-1,4-dione Structure

6944-78-1

3-amino-2-bromo...

~68%

N-(3-bromo-6,7-dimethyl-1,4-dioxo-naphthalen-2-yl)acetamide Structure

72364-90-0

N-(3-bromo-6,7-...

1,4-Naphthalenedione,6,7-dimethyl- Structure

2202-79-1

1,4-Naphthalene...

~%

N-(3-bromo-6,7-dimethyl-1,4-dioxo-naphthalen-2-yl)acetamide Structure

72364-90-0

N-(3-bromo-6,7-...

2,3-dibromo-6,7-dimethyl-naphthalene-1,4-dione Structure

41791-77-9

2,3-dibromo-6,7...

~%

N-(3-bromo-6,7-dimethyl-1,4-dioxo-naphthalen-2-yl)acetamide Structure

72364-90-0

N-(3-bromo-6,7-...

2-acetamido-3-amino-6,7-dimethyl-1,4-naphthoquinone Structure

18691-24-2

2-acetamido-3-a...

~%

6,7-dimethyl-2H-benzo[f]benzotriazole-4,9-dione Structure

72364-91-1

6,7-dimethyl-2H...

4,9-dihydro-6,7-dimethyl-4,9-dioxo-1-(4-methoxybenzyl)naphtho[2,3-d]-v-triazole Structure

79707-03-2

4,9-dihydro-6,7...

~61%

6,7-dimethyl-2H-benzo[f]benzotriazole-4,9-dione Structure

72364-91-1

6,7-dimethyl-2H...

1,4-Naphthalenedione,6,7-dimethyl- Structure

2202-79-1

1,4-Naphthalene...

~%

6,7-dimethyl-2H-benzo[f]benzotriazole-4,9-dione Structure

72364-91-1

6,7-dimethyl-2H...

3-amino-2-bromo-6,7-dimethyl-naphthalene-1,4-dione Structure

6944-78-1

3-amino-2-bromo...

~%

6,7-dimethyl-2H-benzo[f]benzotriazole-4,9-dione Structure

72364-91-1

6,7-dimethyl-2H...

2,3-dibromo-6,7-dimethyl-naphthalene-1,4-dione Structure

41791-77-9

2,3-dibromo-6,7...

~%

6,7-dimethyl-2H-benzo[f]benzotriazole-4,9-dione Structure

72364-91-1

6,7-dimethyl-2H...

N-(3-bromo-6,7-dimethyl-1,4-dioxo-naphthalen-2-yl)acetamide Structure

72364-90-0

N-(3-bromo-6,7-...

~%

6,7-dimethyl-2H-benzo[f]benzotriazole-4,9-dione Structure

72364-91-1

6,7-dimethyl-2H...

N-(3-amino-1,4-dihydroxy-6,7-dimethylnaphthalen-2-yl)acetamide Structure

72365-03-8

N-(3-amino-1,4-...

~%

6,7-dimethyl-2H-benzo[f]benzotriazole-4,9-dione Structure

72364-91-1

6,7-dimethyl-2H...

2H-benzo[f]benzotriazole-4,9-dione Structure

3915-98-8

2H-benzo[f]benz...

~1%

6-nitro-2H-benzo[f]benzotriazole-4,9-dione Structure

72365-05-0

6-nitro-2H-benz...

5-nitro-2H-benzo[f]benzotriazole-4,9-dione Structure

72364-96-6

5-nitro-2H-benz...

1,4-naphthoquinone Structure

130-15-4

1,4-naphthoquinone

~%

5-nitro-2H-benzo[f]benzotriazole-4,9-dione Structure

72364-96-6

5-nitro-2H-benz...

N-(3-amino-1,4-dihydroxynaphthalen-2-yl)acetamide Structure

72365-04-9

N-(3-amino-1,4-...

~%

5-nitro-2H-benzo[f]benzotriazole-4,9-dione Structure

72364-96-6

5-nitro-2H-benz...

1-[(4-methoxyphenyl)methyl]-1H,4H,9H-naphtho[2,3-d][1,2,3]triazole-4,9-dione Structure

79707-02-1

1-[(4-methoxyph...

~%

5-nitro-2H-benzo[f]benzotriazole-4,9-dione Structure

72364-96-6

5-nitro-2H-benz...

1,4-Naphthalenedione,6,7-dimethyl- Structure

2202-79-1

1,4-Naphthalene...

~%

3-amino-2-bromo-6,7-dimethyl-naphthalene-1,4-dione Structure

6944-78-1

3-amino-2-bromo...

2H-benzo[f]benzotriazole-4,9-dione Structure

3915-98-8

2H-benzo[f]benz...

~0%

6-nitro-2H-benzo[f]benzotriazole-4,9-dione Structure

72365-05-0

6-nitro-2H-benz...

5-nitro-2H-benzo[f]benzotriazole-4,9-dione Structure

72364-96-6

5-nitro-2H-benz...

1,4-naphthoquinone Structure

130-15-4

1,4-naphthoquinone

~%

6-nitro-2H-benzo[f]benzotriazole-4,9-dione Structure

72365-05-0

6-nitro-2H-benz...

N-(3-amino-1,4-dihydroxynaphthalen-2-yl)acetamide Structure

72365-04-9

N-(3-amino-1,4-...

~%

6-nitro-2H-benzo[f]benzotriazole-4,9-dione Structure

72365-05-0

6-nitro-2H-benz...

1-[(4-methoxyphenyl)methyl]-1H,4H,9H-naphtho[2,3-d][1,2,3]triazole-4,9-dione Structure

79707-02-1

1-[(4-methoxyph...

~%

6-nitro-2H-benzo[f]benzotriazole-4,9-dione Structure

72365-05-0

6-nitro-2H-benz...


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