170808-74-9Relevant academic research and scientific papers
Revised Structure and Convergent Synthesis of Nemertelline, the Neurotoxic Quaterpyridine Isolated from the Hoplonemertine Sea Worm
Cruskie, Michael P.,Zoltewicz, John A.,Abboud, Khalil A.
, p. 7491 - 7495 (1995)
The correct structure of the quaterpyridine nemertelline first isolated from hoplonemertine sea worms has been identified as 2 (3,2':3',4'':2'',3'''-quaterpyridine).The natural product was synthesized using palladium(0)-catalyzed cross-coupling of 3-(tributylstannyl)-2,3'-bipyridine (3) and 4-chloro-2,3'-bipyridine (4).The bipyridines were prepared in the presence of the Pd catalyst by cross-coupling 2-bromo-3-(tributylstannyl)pyridine (5) and 2,4-dichloropyridine with 3-diethyl(pyridyl)borane, respectively.X-ray analysis confirmed the structure of 2 and provided its conformation in the solid state.The proton NMR spectrum of 2 identifies it as the natural product first reported in 1976.
Some regioselective cross-coupling reactions of halopyridines and halopyrimidines
Simkovsky, Nadja M.,Ermann, Monika,Roberts, Stanley M.,Parry, David M.,Baxter, Andy D.
, p. 1847 - 1849 (2002)
A high yielding approach for the synthesis of bipyridines, pyridylpyrimidines and pyridylquinolines was described. The approach employed regioselective cross-coupling reactions using palladium catalysts. The synthesis involved lithiation of a heterocycle at low temperatures, and eliminated the need to prepare and handle active zinc. The bipyridine group in the compounds exhibits antibiotic and cytotoxic properties and some have potential to be used as fungicides.
