PURINE N-OXIDES. VIII. N-OXIDES OF AZAPURINES

Journal Article · Mon Jun 20 04:00:00 EDT 1960 · Journal of the American Chemical Society (U.S.)

DOI:https://doi.org/10.1021/ja01497a050· OSTI ID:4198904

Stevens, M A; Smith, H W; Brown, G B

Comparisons were made between the behavior of adenine 1-N-oxide and the behavior of the N-oxides of the azaadenines in which the 2- and/or 8-methylidyne groups are replaced by aza groups. 8-Azaadenine is oxidized by peroxyacetic acid to a 1-N-oxide. 2-Azaadenine is oxidized to two hydrolytically stable N-oxides. The structure of the 2-azaadenine N-oxide formed in larger amount is proved to be a 1-N-oxide by an alternative synthesis from 4-aminoimidazole-5-carboxamidoxime and nitrous acid. The structure of the other is unknown. The ribosyl derivative of 4-aminoimidazole-5-carboxamidoxime, obtained by the alkaline hydrolysis of adenosine 1-N-oxide, yields 2azaadenosine 1-N-oxide with nitrous acid. 8- Azaadenine 1-N-oxide, like adenine 1-N-oxide, exhibits hydrolytic instability in the 6-membered ring and yields 4-aminotriazole-5-carboxamidoxime. This latter gives the corresponding carboxamide and carboxamidine upon hydrolysis and hydrogenation, respectively. Upon direct nitrosation this carboxamidoxime yields 2,8-diazaadenine 1-N-oxide. The oxime of the hydrolysis product of 6- methylpurine 1-N-oxide, 4-acetyl-5-aminoimidazole, gives 6-methyl2-azapurine 1-N- oxide upon nitrosation. (auth)

• Research Organization: Sloan-Kettering Inst. for Cancer Research, New York; Cornell Univ. Medical Coll., New York
• Sponsoring Organization: USDOE
• NSA Number: NSA-14-017807
• OSTI ID: 4198904
• Journal Information: Journal of the American Chemical Society (U.S.), Journal Name: Journal of the American Chemical Society (U.S.) Vol. Vol: 82; ISSN JACSA
• Country of Publication: Country unknown/Code not available
• Language: English

Related Subjects

AMIDES
BEHAVIOR
CHEMISTRY
HYDROGENATION
HYDROLYSIS
ORGANIC NITROGEN COMPOUNDS
OXIDES
PURINES