Abstract
Treatment of α-nitro ketone tosylhydrazones with DBU gives 1,4-elimination of nitrous acid affording 1-tosylazoalkenes which, under basic conditions (DBU), tautomerize to the more stable enone tosylhydrazones. The obtained tosylhydrazones may be used as starting material for a wide range of other functionalities. Removal of the hydrazone affords conjugated enones in good yields. Due to the possibility to prepare the nitro ketones with the nitro group in α or α′ position, by this method it is possible to obtain α,β-unsaturated carbonyl compounds with the complete regioselectivity.
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