Makrocyclische Benzolactone durch Ringerweiterung von 2‐Nitrocycloalkanonen

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Abstract
Macrocyclic Benzolactones by Ring Enlargement of 2‐NitrocycloalkanonesReaction of 2‐nitroalkanones with 1,4‐benzoquinone in the presence of 1,8‐diazabicyclo[5.4.0]undec‐7‐en gave (hydroxybenzo)nitrolactones of general formula 6 (Scheme 1). The transformation involves a Michael reaction, aromatization, and ring enlargement via a five‐membered intermediate. The (hydroxybenzo)nitrolactones were converted to the already known (acetoxybenzo)oxolactones 15–17. The characteristic mass spectral behavior of the ring‐enlarged products is discussed.