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

Autor:	Stephen C. Bergmeier, Aravinda B. Pulipaka
Rok vydání:	2008
Předmět:	chemistry.chemical_compound Nucleophile Stereochemistry Chemistry Intramolecular force Intramolecular cyclization General Medicine Aziridine Amaryllidaceae Alkaloids Ring (chemistry)
Zdroj:	ChemInform. 39
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200837138
Popis:	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-1 H-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.
Databáze:	OpenAIRE
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