Synthesis of 6-ethynylpurine derivatives
✍ Scribed by András Nagy; András Kotschy
- Publisher
- Elsevier Science
- Year
- 2008
- Tongue
- French
- Weight
- 116 KB
- Volume
- 49
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A series of 6-(arylethynyl)purine derivatives are synthesized from the corresponding 6-halopurines via sequential and 'one-pot' Sonogashira-coupling reactions. The nature of the acetylene source was found to have a profound influence on the efficiency of the process. In sequential couplings, 2-methyl-but-3-yn-2-ol was found to be an efficient acetylene surrogate, while in the 'one-pot' reaction, 1-ethynylcyclohexanol gave superior results.
📜 SIMILAR VOLUMES
2-BenzyI-N-tert-butoxycarbonyl-1,5-imino-1,2,5-trideoxy-D-xylitol (4) and 5-amino-4benzyl-4,5-dideoxy-L-xylose (13) were prepared in optically pure form.
Cyclotrimerization reactions of the 9-protected 6-ethynylpurines 4a,b in the presence of various transition metal catalysts were studied. The best results were obtained with Ni(COD) 2 or Ni(COD) 2 /PPh 3 to obtain the 1,2,4-and 1,3,5-tris(purin-6-yl)benzenes 5a,b and 6a,b in moderate to good yields