Manganese(III) acetate-mediated peroxycyclization between 2-hydroxy-3-methylnaphthoquinone and various alkenes was performed to obtain dihydronaphtho[2,3-c][1,2]dioxine-5,10(3H,10aH)-diones. The reactivity of symmetrical or unsymmetrical 1,1-disubstituted alkenes and monosubstituted alkenes allowed the synthesis of more than 50 original molecules. Focusing on the excellent reactivity of 2-hydroxy-3-methylnaphthoquinone, we describe the first example of Mn(OAc) 3 reactivity with nitrosubstituted alkenes. The scope, limitations and stereochemistry of the products synthesized are discussed. Starting from monosubstituted alkenes, the instability of a pair of diastereoisomers was observed, leading to ring opening.
An original and short synthesis of substituted 2,3-dihydrobenzo[g]indol-5-ones by S RN 1-mediated synthesis of 2-nitroalkylsubstituted naphthalene-1,4-diones followed by a one-pot reductioncyclization reaction is reported.
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