Synthesis of Hexahydro-1H-benzo[c]chromen-1-amines via the Intramolecular Ring-Opening Reactions of Aziridines by π-Nucleophiles

Aravinda B. Pulipaka; Stephen C. Bergmeier

doi:10.1055/s-2008-1072561

PAPER

Synthesis of Hexahydro-1H-benzo[c]chromen-1-amines via the Intramolecular Ring-Opening Reactions of Aziridines by π-Nucleophiles

Aravinda B. Pulipaka, Stephen C. Bergmeier*
Department of Chemistry & Biochemistry, Clippinger Laboratory, Ohio University, Athens, OH 45701, USA
e-Mail: bergmeis@ohio.edu;

Abstract

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Abstract

The intramolecular cyclization of aziridines with π-nucleophiles can be a useful route to a number of heterocyclic and carbocyclic systems. This methodology has been applied to the synthesis of hexahydro-1H-benzo[c]chromen-1-amines, the basic skeleton of many amaryllidaceae alkaloids. The success of the aziridine cyclization is largely dependent on the N-substitution of aziridine, with activated aziridines not undergoing the cyclization reaction. Only N-H-, N-alkyl- and N-arylaziridines underwent the cyclization reaction. The ring opening of an unactivated aziridines with a π-nucleophile is one of the first examples of such a reaction.

Key words

heterocycles - electrophilic additions - ring opening - ethers - amines

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References

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