Purines. V. Reaction of 9-phenyl-9H-purine-6-carbonitrile with nucleophilic reagents.

• HIGASHINO TAKEO

• YOSHIDA SHIZUO

• HAYASHI EISAKU

Abstract

The reaction of 9-phenyl-9H-purine-6-carbonitrile (1) with nucleophilic reagents occurred by addition of the reagent across the C-N triple bond of the cyano group, and substitution of the cyano group was not observed. Thus, the reactions with hydroxylamine, hydrazine, amines, Grignard reagents, and 98% sulfuric acid gave the corresponding amidoxime (2), amidorazone (3), amidines (4), ketones (5), and amide (7), respectively. Alcoholysis of 1 gave the ester (6) and 7 together with the ring fission product of the imidazole portion, alkyl 5-amino-6-anilino-4-pyrimidine-carboxylate (8). Amides (10), the hydroxamic acid (11), and the hydrazide (12) were prepared from the methyl ester (6a).

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 30 (12), 4521-4525, 1982

  The Pharmaceutical Society of Japan

Keywords

• nucleophilic reagent

Details

• CRID: 1390282679141689216
• NII Article ID: 130003769065
• DOI: 10.1248/cpb.30.4521
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/30/12/30_12_4521/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed