Advanced Synthesis and Catalysis p. 553 - 563 (1997)
Update date:2022-08-04
Demir, Ayhan S.
Enders, Dieter
Cyclic 1,3- diketones 1 are transformed into their 2,2-dimethylhydrazones 2, which can be alkylated regioselectively at different positions after mono-, di-, tri-, and tetrametalation. Monometalated C-2 unsubstituted hydrazones afford C-2 and N- alkylation, monometalated C-2 substituted hydrazones afford only C-2 alkylation.The regioselectivity of the alkylation of the polymetalated hydrazones follows Hauser's rule according to the sequence: NH- > C-4 Ha > C-5 > C-4 Hb. Hydrolysis of the product hydrazones 3-5 afforded mono- and polyalkylated 1,3- diketones 7 in good yields.
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