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DOI: 10.1055/s-0036-1588713
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
Publication History
Received: 22 November 2016
Accepted after revision: 20 January 2017
Publication Date:
14 February 2017 (online)
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 oilSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588713.
- Supporting Information
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