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■ Metalation of Pyrazinethiocarboxamides. Metalation of Diazines XXVI

Corinne Fruit, Alain Turck, Nelly Plé, and Guy Quéguiner*

*Laboratoire de Chimie Organique Fine et Hétérocyclique(UPRES-A 6014), IRCOF, INSA, Université de Rouen, Place Emilae Blondel, BP 08,76131 Mont-Saint-Aignan Cedex, France

Abstract

Some new pyrazinethiocarboxamides were synthesized and metalated with LTMP in tetrahydrofuran. The reaction of these lithio derivatives with various electrophiles gave access to a large range of 2,5-disubstituted pyrazines. This unexpected regioselectivity was established by application of gradient enhanced HMBC sequence for the observation of long range ¹H-¹⁵N heteronuclear couplings at natural abundance.