1999 alkylation, arylation, dealkylation, dearylation, C-acylation, olefination

alkylation, arylation, dealkylation, dearylation, C-acylation, olefinationO 0280

24 - 058Direct Conversion of Heteroaromatic Esters to Methyl Ketoneswith Trimethylaluminum: Nonsymmetrically Disubstituted 1,2,4,5-Tetrazines. — Esters (I) of nitrogen heterocycles readily react with AlMe3to give the corresponding methyl ketones. Interestingly, unsymmetricallysubstituted diester [cf. (Id)] provides (IIId) completely regioselectively. Initialcomplexation of the aluminum reagent with the neighboring ring nitrogen maybe operating, explaining the lack of reactivity with dinitrobenzoate ester (Ie).— (GIRARDOT, MARC; NOMAK, RANA; SNYDER, JOHN K.; J. Org.Chem. 63 (1998) 26, 10063-10068; Dep. Chem., Boston Univ., Boston, MA02215, USA; EN)

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