Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Communication | Regular issue | Vol 57, No. 12, 2002, pp.2231-2237
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9634
Synthesis, Tautomerism and Calculations of Mesomeric Betaines of Guanine

Andreas Schmidt* and Nikoloz Kobakhidze

*Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany

Abstract

Reaction of purine-N-oxide (4) with 4-(dimethylamino)pyridine and acetyl chloride, followed by the treatment with hydrochloric acid gave the purinepyridinium salt (6) which was deprotonated to the mesomeric betaine (7). Depending on the reaction conditions, 4-methylpyridine and pyridine, respectively, converted the nucleoside (8) into the pyridinium salts (9) and (10), or into the mesomeric betaines (11) and (12). According to calculations, the conjugated tautomers (A-D) of betaine (7) are more stable than the cross-conjugated tautomer (7E).