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Oxidation of 7,8-diaminotheophylline with lead tetraacetate and reaction of the oxidation product, 6-cyanoimino-5-diazo-1,3-dimethylpyrimidine-2,4-dione with alcohols or amines

✍ Scribed by Taisei Ueda; Naoyoshi Yatsuzuka; Shin-Ichi Nagai; Kumiko Okada; Emi Takeichi; Hiromi Segi; Jinsaku Sakakibara

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
62 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Oxidation of 7,8‐diaminotheophylline (1) with lead tetraacetate in refluxing toluene gave a mixture of 3‐amino‐5,7‐dimethylpyrimido[4,5‐e][1,2,4]triazine‐6,8‐dione (2) and 6‐cyanoimino‐5‐diazo‐1,3‐dimethylpyrimidine‐2,4‐dione (4). The latter was transformed to 2 by the reaction with 1‐propanethiol in quantitative yield. The reaction of 4 with methanol, ethanol and 1‐propanol in the presence of rhodium (II) acetate gave 5‐alkoxy‐6‐(2‐alkyl‐3‐isoureido)‐1,3‐dimethylpyrimidine‐2,4‐diones (7a‐c). A similar reaction of 4 with alkylamines such as n‐propylamine, n‐butylamine, isobutylamine and n‐hexylamine gave a mixture of 7‐alkyl‐8‐aminotheophyllines (8a‐d) and (5‐alkylamino‐1,3‐dimethyl‐2,4‐dioxopyrimidin‐6‐yl)cyanamides (9a‐d).

📜 SIMILAR VOLUMES

ChemInform Abstract: Oxidation of 7,8-Di
ChemInform Abstract: Oxidation of 7,8-Diaminotheophylline with Lead Tetraacetate and Reaction of the Oxidation Product, 6-Cyanoimino-5-diazo-1,3-dimethylpyrimidine-2,4-dione with Alcohols or Amines.
✍ Taisei Ueda; Naoyoshi Yatsuzuka; Shin-ichi Nagai; Kumiko Okada; Emi Takeichi; Hi 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 2 views

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