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Paper | Regular issue | Vol 51, No. 10, 1999, pp.2349-2365
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8625
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


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.