Tetrahedron

A novel reactivity of α-nitro ketone tosylhydrazones with DBU. Synthesis of α, β-unsaturated enone tosylhydrazones

R Ballini, G Giantomassi

Index: Ballini, Roberto; Giantomassi, Gianni Tetrahedron, 1995 , vol. 51, # 14 p. 4173 - 4182

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Citation Number: 6

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 ...