184938

SYNTHESIS OF SOME NEW IMIDAZOLIUM AND PURINIUM SALTS AND THEIR RELATED DERIVATIVES

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Last updated: 04 Jan 2025

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Abstract

Cyclization of 5-amino-1-(4-methoxyphenyl) imidazole-4-carbonitrile 3 with formamide afforded 6-aminopurine derivative 4. When the latter was reacted with alkyl iodides, the purinium iodide salts 7a-c were obtained. Upon treating the salts 7a-c with a - kali, the dequaternized and rearranged products N-alkyl-9-(4-methoxyphenyl)-6-amino-9H-purina 8a-c were obtained. The 5- (methoxymethylideneamino) imidazole-4- carbonitrile 10 was synthesized by reacting 3 with trimethyl orthoformate. When the imidate 10 reacted with alkylamines, the corresponding 1-alkyl-9- (4-methoxyphenyl)-6-imino-9H-purines 1la-c were obtained. Rearrangement of the products 11a-c to their N-alkyl-6-amino-9H-purines 8a-c was carried out. The 3-alkylimidazolium-4-carbonitrile iodides 12a-e were synthesized by quaternizing product 3 with alkyl iodides. Treatment of the salts 12a-e with alkali, afforded the ring-opened products : 2-amino-2-(4-methoxyphenylamino)-1-N-alkyl formylaminoethylene-1-carbonitriles 13a-e, rather than the expected 1-alkyl-4-(4-methoxyphenylamino) imidazole-5-carbonitriles 14a-e. Products 14a-e were obtained by cyclization of 13a-e in acidic medium.

DOI

10.21608/zjps.1997.184938

Authors

First Name

Wahid

Last Name

Basyouni

MiddleName

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Affiliation

Pesticide Chemistry Department, National Research Centre, Dokki, Cairo, Egypt.

Email

wahid.basyouni@yahoo.com

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Orcid

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Volume

6

Article Issue

2

Related Issue

24768

Issue Date

1997-12-01

Receive Date

1997-08-03

Publish Date

1997-12-01

Page Start

14

Page End

22

Print ISSN

1110-5089

Online ISSN

2356-9786

Link

https://zjps.journals.ekb.eg/article_184938.html

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https://zjps.journals.ekb.eg/service?article_code=184938

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4

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Original Article

Type Code

862

Publication Type

Journal

Publication Title

Zagazig Journal of Pharmaceutical Sciences

Publication Link

https://zjps.journals.ekb.eg/

MainTitle

SYNTHESIS OF SOME NEW IMIDAZOLIUM AND PURINIUM SALTS AND THEIR RELATED DERIVATIVES

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Article

Created At

22 Jan 2023