The regioselectivity of the metalation of 2‐chloro‐6‐methoxypyrazine, 2‐fluoro‐6‐methoxypyrazine and 3‐fluoro‐6‐chloropyridazine was studied; the relative ortho‐directing power was F > OMe > Cl.
Pyrazine derivativesPyrazine derivatives R 0550 Regioselective Synthesis and Metalation of Tributylstannylfluoropyrazines. Application to the Synthesis of Some New Fluorinated Liquid Crystals Diazines. Part 34. -A general synthetic route to various 3-alkyl-6-arylpyrazine [cf. (VIII)] and 3,6-diarylpyrazine derivatives [cf. (X), (XI)] involving regioselective metalation and Pd-catalyzed cross-coupling steps starting from fluoropyrazine (I) is developed. Some diarylpyrazines such as (XI), which are linear aza analogues of terphenyl, display liquid-crystalline properties. -(TOUDIC, F.; HEYNDERICKX, A.; PLE*, N.; TURCK, A.; QUEGUINER, G.; Tetrahedron 59 (2003) 33, 6375-6384; Lab. Chim. Org. Fine Heterocycl., IRCOF, Inst. Natl. Sci. Appl. Rouen, F-76131 Mont-Saint-Aignan, Fr.; Eng.) -M. Schroeter 49-139
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