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

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 ...

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

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

~%

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

8-(4-methylphen...

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p-toluoyl chloride Structure

p-toluoyl chloride

~%

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

8-(4-methylphen...

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

N1-(p-methylphe...

~%

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

8-(4-methylphen...

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

6H-Purin-6-imin...

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

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

~%

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

8-(4-methylphen...

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

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

~%

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

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

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

N1-(p-methylphe...

~%

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

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

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

6H-Purin-6-imin...

~%

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

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

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Structure

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

6H-Purin-6-imin...

~%

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

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

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((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

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

~0%

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

8-(4-bromopheny...

5'-Adenylic acid Structure

5'-Adenylic acid

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

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

2-Naphthol Structure

~92%

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

6H-Purin-6-imin...

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

1-[(4-bromophen...

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

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

~15%

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

8-(4-bromopheny...

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

6H-Purin-6-imin...

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(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

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

~11%

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

8-(4-bromopheny...

Adenosine Structure

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((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

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

~14%

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

8-(4-bromopheny...

5'-Adenylic acid Structure

5'-Adenylic acid

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

6H-Purin-6-imin...

~%

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

8-(4-bromopheny...

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

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

~19%

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

8-(4-bromopheny...

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

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

~%

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

8-(4-bromopheny...

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

N1-(p-methylphe...

~%

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

8-(4-bromopheny...

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4-Bromobenzoyl chloride Structure

4-Bromobenzoyl ...

~%

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

8-(4-bromopheny...

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

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

2,6-Diaminopurine Structure

2,6-Diaminopurine

~%

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

8-(4-bromopheny...

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

8-(4-bromopheny...

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

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

~%

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

8-(4-bromopheny...

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(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

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

~0%

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

8-(4-bromopheny...

Adenosine Structure

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4,5,6-Pyrimidinetriamine sulfate Structure

4,5,6-Pyrimidin...

Benzoyl chloride Structure

Benzoyl chloride

~%

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

Benzamide,N-(4,...

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C 8-Arylguanine and C 8-aryladenine formation in calf thymus...

[Gannett, Peter M.; Powell, Jeannine H.; Rao, Ramakrishna; Shi, Xiangling; Lawson, Terence; Kolar, Carol; Toth, Bela Chemical Research in Toxicology, 1999 , vol. 12, # 3 p. 297 - 304]

C 8-Arylguanine and C 8-aryladenine formation in calf thymus...

[Gannett, Peter M.; Powell, Jeannine H.; Rao, Ramakrishna; Shi, Xiangling; Lawson, Terence; Kolar, Carol; Toth, Bela Chemical Research in Toxicology, 1999 , vol. 12, # 3 p. 297 - 304]