Synthesis of Chiral C2-Symmetric 1,10-Phenanthrolines from Naturally Occurring Monoterpenes

Giorgio Chelucci; Giovanni Loriga; Gabriele Murineddu; Gerard A. Pinna

doi:10.1055/s-2003-36260

PAPER

Synthesis of Chiral C₂-Symmetric 1,10-Phenanthrolines from Naturally Occurring Monoterpenes

Giorgio Chelucci*^a, Giovanni Loriga^b, Gabriele Murineddu^b, Gerard A. Pinna^b
^a Dipartimento di Chimica, Università di Sassari, via Vienna 2, 07100 Sassari, Italy
Fax: +39(79)229559; e-Mail: chelucci@ssmain.uniss.it;
^b Dipartimento Farmaco Chimico Tossicologico, Università di Sassari, Via Muroni 23, 07100 Sassari, Italy

Abstract

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Abstract

A convenient procedure for the preparation of chiral C₂-symmetric 1,10-phenanthrolines bearing a chiral framework in the form of a cycloalkeno-condensed substituent in the 2,3- and 8,9-positions of the heterocycle is reported. Starting from the 2-benzyloxycyclohexanone, four 1,10-phenanthrolines derived from (-)-β-pinene, (+)-α-pinene, (-)-isopinocampheol, and (+)-camphor were prepared according to a method based on a double Michael-azaannulation-aromatization sequence.

Key words

nitrogen heterocycles - 1,10-phenanthrolines - nitrogen ligands - bidentate ligands - Michael additions

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Referenzen

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