Synthesis of New 2-Azaadenines and 2-Azahypoxanthines from 4-Diazo-4H-imidazoles

✍ Scribed by Andersen, Knud Erik ;Pedersen, Erik B.

• Publisher: John Wiley and Sons
• Year: 1986
• Tongue: English
• Weight: 469 KB
• Volume: 1986
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.198619860606

✦ Synopsis

Amino-I H-imidazole-4-carboxamide hydrochloride has been converted into a series of new, potentially biologically active N6-substituted 2-azaadenines 5 via 4-diazo-4H-imidazole-5-carbonitrile (1) which was coupled with primary amines to give 5 in 11 -78% yield. Further, some I-substituted 2-azahypoxanthines 9 have been prepared in 17 -66% yield from ethyl 5-amino-I H-imidazole-4-carboxylate (6) via ethyl 4-diazo-4ff-imiddzok-5-cdrboxylate (7) which was coupled with primary amines.

Synthese neuer 2-Azaadenine und 2-Azahypoxanthine aus 4-Diazo-4H-imidazolen

Eine Reihe neuer, moglicherweise biologisch wirksamer N6-substituierter 2-Azaadenine 5 wurde aus 5-Amino-I H-imidazol-4-carboxamid-hydrochlorid iiber 4-Diazo-4H-imidazol-5carbonitril (I), das mit primaren Aminen gekuppelt wurde, rnit 31 -78proz. Ausbeute hergestellt. Auch einige I-substituierte 2-Azahypoxanthine 9 wurden aus 5-Amino-Iff-imidazol-4-carbonsiure-ethylester (6) iiber 4-Diazo-4H-imidazol-5-carbonsaure-ethylester (7) durch Kopplung mit primaren Aminen mit 17 -66proz. Ausbeute gewonnen.