Highly Diastereoselective Synthesis of New trans-Fused Octahydro­acridines via Intramolecular Cationic Imino Diels–Alder Reaction of N-Protected Anilines and Citronellal or Citronella Essential Oil

Abstract

The one-pot diastereoselective synthesis of new N-substituted octahydroacridines was successfully achieved via BiCl₃-catalyzed intramolecular cationic imino Diels–Alder reaction in good yields employing N-protected anilines and (±)-citronellal as substrates under mild conditions. It was observed that bulky N-substituent groups (allyl, propargyl, and benzyl substituent) play a key role in the cis/trans ratio of the thus-formed octahydroacridines. Increasing bulkiness permits preferential formation of the trans-fused heterocycles. It was found that use of the N-benzyl group resulted in a highly diastereoselective process that gives easily separable trans-fused N-substituted octahydroacridines. The developed protocol was extended to involve the use of citronella essential oil from Cymbopogon nardus as a renewable source of these biologically important heterocyclic molecules.

Key words

octahydroacridines - diastereoselective synthesis - cationic imino Diels–Alder reaction - citronella essential oil

• References

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