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A New Synthesis of Pteridines
✍ Scribed by Ming Xu; Andrea Vasella
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- German
- Weight
- 86 KB
- Volume
- 89
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
A new synthesis of pteridines possessing a (substituted) (Z)‐3‐hydroxyprop‐1‐enyl group at C(6) is based on the acylation of 4‐amino‐5‐nitrosopyrimidines with dienoic acid chlorides, followed by a high‐yielding intramolecular hetero‐Diels–Alder cycloaddition and cleavage of the NO bond leading to 4. Thermolysis of the resulting pteridines 4 possessing a benzyloxy group at C(4) led to the products 5, resulting from isomerisation of the 3‐hydroxyprop‐1‐enyl to an 3‐oxopropyl side chain, while the analogous pteridine 8 possessing an NH~2~ group at C(4) remained unaffected.
📜 SIMILAR VOLUMES
## Abstract Reaction of 2‐aminopyrazine 1 with isothiocyanate, isocyanate or dithioketal reagent furnished pteridines **3,4** in good yield. Thioxo compound **3a** was chlorinated, methylated and subsequently displaced by amines. A simple one‐step synthesis of heterocondensed pteridines **8–13** by
## Abstract Pteridines substituted with a 1,1‐, 1,2‐, or 1,1,3‐substituted alkenyl group (mostly (__E__)‐configured) at C(6) were synthesized in high yields by the intramolecular nitroso‐ene reaction of 4‐(alkenoylamino)‐2‐amino‐6‐benzyloxy‐5‐nitroso‐ and 4‐(alkenoylamino)‐2,6‐diamino‐5‐nitrosopyri
## Abstract A variety of pyrimidine precursors **12**–**25** were converted into a series of new 7‐hydroxylumazines (=7‐hydroxypteridine‐2,4(1__H__,3__H__)‐diones) **26**–**35** which functioned as starting materials for the transformation into the corresponding 7‐chlorolumazines **36**–**45**. Sub