Cocyclotrimerization of 6-alkynylpurines with alpha,omega-diynes as a novel approach to biologically active 6-arylpurines.
Transition metal complex catalyzed cocyclotrimerization of 6-alkynylpurines 1 with various diynes enables the preparation of a plethora of substituted 6-arylpurines 3 in good yields. The most general catalyst for the reaction is a user-friendly system based on a nickel-phosphine complex and reductant (NiBr(2)(dppe)/Zn) in MeCN. The reaction conditions are compatible with various protective groups on the purine moiety (Bn, THP). As far as other potential catalysts were concerned, only CoBr(PPh(3))(3) showed reasonable activity in cocyclotrimerization of alkynylpurines with dipropargyl ether. A comparison of catalytic with stoichiometric approaches and the ligand effect in the catalyst is also given. Cytostatic activity screening of title 6-arylpurines was performed and several moderately active compounds were found.
Turek
Pavel
P
Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Prague 2, Czech Republic.
Kotora
Martin
M
Tislerová
Iva
I
Hocek
Michal
M
Votruba
Ivan
I
Císarová
Ivana
I
D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011108:Polymers / Q000737:chemistry*; D011687:Purines / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D011108:Polymers; D011687:Purines