The Journal of Organic Chemistry

Reactions of benzenediazonium ions with adenine and its derivatives

A Chin, MH Hung, LM Stock

Index: Chin, Anton; Hung, Ming-Hong; Stock, Leon M. Journal of Organic Chemistry, 1981 , vol. 46, # 11 p. 2203 - 2207

Full Text: HTML

Citation Number: 63

Abstract

Adenine, adenosine, and 5'-adenylic acid react readily with benzenediazonium ion and its derivatives at pH 8-11 to yield derivatives of (E)-6-(3-phenyl-2-triazen-l-yl) purine. The structural assignments for these compounds, some of which are unstable, are based on their spectroscopic properties and their degradation reactions in acid solution and with sodium dithionite to yield 6-hydrazinopurine. The triazenes decompose in basic aqueous solution ...

 Related Synthetic Route
(E)-6-[3-(4-Bromophenyl)-2-triazen-1-yl]purine Structure

77070-97-4

(E)-6-[3-(4-Bro...

~%

8-(4-methylphenyl)-7H-purin-6-amine Structure

77071-03-5

8-(4-methylphen...

p-toluoyl chloride Structure

874-60-2

p-toluoyl chloride

~%

8-(4-methylphenyl)-7H-purin-6-amine Structure

77071-03-5

8-(4-methylphen...

N1-(p-methylphenyl)-N3-purinyltriazene Structure

112177-84-1

N1-(p-methylphe...

~%

8-(4-methylphenyl)-7H-purin-6-amine Structure

77071-03-5

8-(4-methylphen...

6H-Purin-6-imine, 1,7-dihydro- (9CI) Structure

66224-66-6

6H-Purin-6-imin...

N-(7H-purin-6-yldiazenyl)aniline Structure

112177-85-2

N-(7H-purin-6-y...

~%

8-(4-methylphenyl)-7H-purin-6-amine Structure

77071-03-5

8-(4-methylphen...

(E)-6-[3-(4-Bromophenyl)-2-triazen-1-yl]purine Structure

77070-97-4

(E)-6-[3-(4-Bro...

~%

N-(7H-purin-6-yldiazenyl)aniline Structure

112177-85-2

N-(7H-purin-6-y...

N1-(p-methylphenyl)-N3-purinyltriazene Structure

112177-84-1

N1-(p-methylphe...

~%

N-(7H-purin-6-yldiazenyl)aniline Structure

112177-85-2

N-(7H-purin-6-y...

6H-Purin-6-imine, 1,7-dihydro- (9CI) Structure

66224-66-6

6H-Purin-6-imin...

~%

N-(7H-purin-6-yldiazenyl)aniline Structure

112177-85-2

N-(7H-purin-6-y...

Structure

74497-02-2

6H-Purin-6-imine, 1,7-dihydro- (9CI) Structure

66224-66-6

6H-Purin-6-imin...

~%

N-(7H-purin-6-yldiazenyl)aniline Structure

112177-85-2

N-(7H-purin-6-y...

((2R,3S,4R,5R)-5-(6-((E)-3-(4-bromophenyl)triaz-2-en-1-yl)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate Structure

77079-61-9

((2R,3S,4R,5R)-...

~0%

8-(4-bromophenyl)-7H-purin-6-amine Structure

77071-04-6

8-(4-bromopheny...

5'-Adenylic acid Structure

61-19-8

5'-Adenylic acid

(E)-6-[3-(4-Bromophenyl)-2-triazen-1-yl]purine Structure

77070-97-4

(E)-6-[3-(4-Bro...

2-Naphthol Structure

135-19-3

2-Naphthol

~92%

6H-Purin-6-imine, 1,7-dihydro- (9CI) Structure

66224-66-6

6H-Purin-6-imin...

1-[(4-bromophenyl)hydrazinylidene]naphthalen-2-one Structure

7150-24-5

1-[(4-bromophen...

(E)-6-[3-(4-Bromophenyl)-2-triazen-1-yl]purine Structure

77070-97-4

(E)-6-[3-(4-Bro...

~15%

8-(4-bromophenyl)-7H-purin-6-amine Structure

77071-04-6

8-(4-bromopheny...

6H-Purin-6-imine, 1,7-dihydro- (9CI) Structure

66224-66-6

6H-Purin-6-imin...

(2R,3R,4S,5R)-2-(6-((E)-3-(4-bromophenyl)triaz-2-en-1-yl)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol Structure

77071-01-3

(2R,3R,4S,5R)-2...

~11%

8-(4-bromophenyl)-7H-purin-6-amine Structure

77071-04-6

8-(4-bromopheny...

Adenosine Structure

58-61-7

Adenosine

((2R,3S,4R,5R)-5-(6-((E)-3-(4-bromophenyl)triaz-2-en-1-yl)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate Structure

77079-61-9

((2R,3S,4R,5R)-...

~14%

8-(4-bromophenyl)-7H-purin-6-amine Structure

77071-04-6

8-(4-bromopheny...

5'-Adenylic acid Structure

61-19-8

5'-Adenylic acid

6H-Purin-6-imine, 1,7-dihydro- (9CI) Structure

66224-66-6

6H-Purin-6-imin...

~%

8-(4-bromophenyl)-7H-purin-6-amine Structure

77071-04-6

8-(4-bromopheny...

4,6-diamino-5-[(4-bromobenzoyl)amino]pyrimidine Structure

77071-06-8

4,6-diamino-5-[...

~19%

8-(4-bromophenyl)-7H-purin-6-amine Structure

77071-04-6

8-(4-bromopheny...

N-(7H-purin-6-yldiazenyl)aniline Structure

112177-85-2

N-(7H-purin-6-y...

~%

8-(4-bromophenyl)-7H-purin-6-amine Structure

77071-04-6

8-(4-bromopheny...

N1-(p-methylphenyl)-N3-purinyltriazene Structure

112177-84-1

N1-(p-methylphe...

~%

8-(4-bromophenyl)-7H-purin-6-amine Structure

77071-04-6

8-(4-bromopheny...

4-Bromobenzoyl chloride Structure

586-75-4

4-Bromobenzoyl ...

~%

8-(4-bromophenyl)-7H-purin-6-amine Structure

77071-04-6

8-(4-bromopheny...

(E)-6-[3-(4-Bromophenyl)-2-triazen-1-yl]purine Structure

77070-97-4

(E)-6-[3-(4-Bro...

2,6-Diaminopurine Structure

1904-98-9

2,6-Diaminopurine

~%

8-(4-bromophenyl)-7H-purin-6-amine Structure

77071-04-6

8-(4-bromopheny...

8-(4-bromophenyl)-2,6-diaminopurine Structure

77071-05-7

8-(4-bromopheny...

(E)-6-[3-(4-Bromophenyl)-2-triazen-1-yl]purine Structure

77070-97-4

(E)-6-[3-(4-Bro...

~%

8-(4-bromophenyl)-7H-purin-6-amine Structure

77071-04-6

8-(4-bromopheny...

(2R,3R,4S,5R)-2-(6-((E)-3-(4-bromophenyl)triaz-2-en-1-yl)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol Structure

77071-01-3

(2R,3R,4S,5R)-2...

~0%

8-(4-bromophenyl)-7H-purin-6-amine Structure

77071-04-6

8-(4-bromopheny...

Adenosine Structure

58-61-7

Adenosine

4,5,6-Pyrimidinetriamine sulfate Structure

49721-45-1

4,5,6-Pyrimidin...

Benzoyl chloride Structure

98-88-4

Benzoyl chloride

~%

Benzamide,N-(4,6-diamino-5-pyrimidinyl)- Structure

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Benzamide,N-(4,...


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