Volume 32, Issue 45
Isocyclic Compounds
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ChemInform Abstract: A Convenient Synthesis of Alkyl- and Dialkylphenanthren-9-ylamines.

Christophe Hoarau

Christophe Hoarau

Lab. Chim. Org. Phys., CNRS, Univ. Sci. Technol. Lille-Flandres-Artois, F-59655 Villeneuve d′Ascq, Fr.

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Axel Couture

Axel Couture

Lab. Chim. Org. Phys., CNRS, Univ. Sci. Technol. Lille-Flandres-Artois, F-59655 Villeneuve d′Ascq, Fr.

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Eric Deniau

Eric Deniau

Lab. Chim. Org. Phys., CNRS, Univ. Sci. Technol. Lille-Flandres-Artois, F-59655 Villeneuve d′Ascq, Fr.

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Pierre Grandclaudon

Pierre Grandclaudon

Lab. Chim. Org. Phys., CNRS, Univ. Sci. Technol. Lille-Flandres-Artois, F-59655 Villeneuve d′Ascq, Fr.

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First published: 23 May 2010

Abstract

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ChemInform Abstract

A general and convenient synthesis of the title dialkylphenanthrylamines (VI) and (VIII) is presented, involving the radical cyclization of E-diaryleneamines, generated by Horner reaction of phosphane oxides (IVa)—(IVd) or phosphonates like (IVe) with aromatic aldehydes (V). Reductive N-debenzylation of the obtained dialkylphenanthrylamines using HCOONH4—Pd-C provides the corresponding N-monoalkyl analogues (VII).

chemical structure image

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