Nitrosative Adenine Deamination: Facile Pyrimidine Ring-Opening in the Dediazoniation of Adeninediazonium Ion

Author

Brian Hodgen
Sundeep Rayat
Rainer Glaser, Missouri University of Science and TechnologyFollow

Abstract

Dediazoniation of adeninediazonium ion, 1, forms the heteroaromatic cation, 2. Ab initio studies at the CCSD(fc)/6-31G**/ /MP2(full)/6-31G** level now reveal that the cyclic cation 2 is kinetically and thermodynamically unstable with respect to the pyrimidine ring-opened cation, 3. The results suggest that 4-cyano-5-isocyano-imidazole, 4, and 4,5-dicyanoimidazole, 5, might be formed to some extent in nitrosative deaminations of adenine.

Recommended Citation

B. Hodgen et al., "Nitrosative Adenine Deamination: Facile Pyrimidine Ring-Opening in the Dediazoniation of Adeninediazonium Ion," Organic Letters, vol. 5, no. 22, pp. 4077 - 4080, American Chemical Society (ACS), Oct 2003.

The definitive version is available at https://doi.org/10.1021/ol035526d

Department(s)

Chemistry

Keywords and Phrases

4 cyano 5 isocyanoimidazole; 4 dicyanoimidazole; 4,5 dicyanoimidazole; 5 dicyanoimidazole; adenine derivative; imidazole derivative; pyrimidine derivative; unclassified drug; kinetics; nitrosation; ring opening; thermodynamics; Adenine; Deamination; Diazonium Compounds; Imidazoles; Models; Chemical; Models; Molecular; Molecular Structure; Thermodynamics

International Standard Serial Number (ISSN)

1523-7060

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2003 American Chemical Society (ACS), All rights reserved.

Publication Date

01 Oct 2003