Modular, Step-Efficient Palladium-Catalyzed Cross-Coupling Strategy To Access C6-Heteroaryl 2-Aminopurine Ribonucleosides
作者： Helena S. Buchanan , Steven M. Pauff , Tilemachos D. Kosmidis , Andrea Taladriz-Sender , Olivia I. Rutherford
DOI: 10.1021/ACS.ORGLETT.7B01602
关键词: Palladium 、 Boron 、 Ribonucleoside 、 Chemistry 、 Combinatorial chemistry 、 Molecule 、 Sonogashira coupling 、 Organic chemistry 、 Catalysis 、 Azide 、 Coupling
摘要: Two Pd-catalyzed methods to access 6-heteroaryl 2-aminopurine ribonucleosides from 6-chloroguanosine are described. First, Pd-132-catalyzed Suzuki-Miyaura cross-coupling using a series of boron substrates and forms 6-heteroaryl-2-aminopurines in single step. The versatility is further demonstrated modified Sonogashira coupling employing potassium iodide as an additive. Finally, the utility 6-alkynyl-2-aminopurine ribonucleoside dipolarophile [3 + 2] cycloadditions presented, affording triazoles isoxazoles when reacted with azide isonitrile 1,3-dipoles, respectively.
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