Polyfunctionalized Aryllead Triacetates in a Cascade Synthesis of Tetracyclic Isochromanocoumarin-Type Compounds

Mikael I. Naumov; Olga G. Ganina; Andrew S. Shavirin; Irina P. Beletskaya; Jean-Pierre Finet; Alexey Yu Fedorov

doi:10.1055/s-2005-861834

PAPER

Polyfunctionalized Aryllead Triacetates in a Cascade Synthesis of Tetracyclic Isochromanocoumarin-Type Compounds

Mikael I. Naumov^a, Olga G. Ganina^a,b, Andrew S. Shavirin^c, Irina P. Beletskaya^b, Jean-Pierre Finet*^d, Alexey Yu. Fedorov*^a
^a Department of Chemistry, Nizhny Novgorod State University, 23 Gagarin Avenue, 603950 Nizhnii Novgorod, Russia
Fax: +7(8312)658592; e-Mail: afnn@rambler.ru;
^b Department of Chemistry, Moscow State Lomonosov University, Vorobyevy Gory, 119992 Moscow, Russia
e-Mail: beletska@org.chem.msu.ru;
^c G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 Tropinina st., 603600 Nizhnii Novgorod, Russia
Fax: +7(8312)127497; e-Mail: andrew@imoc.sinn.ru;
^d UMR - CNRS 6517, Universités d’Aix-Marseille 1, 2 et 3, Faculté des Sciences Saint-Jérôme, 13397 Marseille Cedex 20, France
Fax: +33(4)91288758; e-Mail: finet@srepir1.univ-mrs.fr;

Abstract

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Abstract

The three-step one-pot α-arylation-annulation sequence leading to the reaction of 4-hydroxycoumarins with in situ generated 2-(bromomethyl)aryllead triacetates carried out in the presence of a combination of ortho-phenantroline-potassium tert-butoxide afforded tetracyclic benzo[b]pyran compounds in good to high yields.

Key words

4-hydroxycoumarins - arylboronic acids - aryllead triacetates - reductive ligand coupling reactions

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