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Cyclotrimerization of 6-ethynylpurines. Synthesis of 1,2,4- and 1,3,5-tris(purin-6-yl)benzenes as novel Hoogsteen-triplet analogues

✍ Scribed by Michal Hocek; Irena G Stará; Ivo Starý; Hana Dvořáková

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
73 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 (in a 4:1 to 10:1 ratio). This method is suitable for the practical synthesis of the unsymmetrical 1,2,4-tris(purin-6-yl)benzenes 5a-c, while the symmetrical 1,3,5-tris(purin-6-yl)benzenes 6a,b are generally formed as minor products.

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