2-(Azidomethyl)arylboronic Acids
in the Synthesis of Coumarin-Type Compounds

Mikael I. Naumov; Alexander V. Nuchev; Nikolay S. Sitnikov; Yulia B. Malysheva; Andrew S. Shavyrin; Irina P. Beletskaya; Andrei E. Gavryushin; Sebastien Combes; Alexey Yu. Fedorov

doi:10.1055/s-0028-1088058

PAPER

2-(Azidomethyl)arylboronic Acids in the Synthesis of Coumarin-Type Compounds

Mikael I. Naumov^a, Alexander V. Nuchev^a, Nikolay S. Sitnikov^a, Yulia B. Malysheva^a, Andrew S. Shavyrin^b, Irina P. Beletskaya^c, Andrei E. Gavryushin^d, Sebastien Combes^e, Alexey Yu. Fedorov*^a
^a Department of Organic Chemistry, Nizhnii Novgorod N. I. Lobachevsky State University, 23 Gagarin Avenue, 603950 Nizhnii Novgorod, Russian Federation
Fax: +7(831)4658592; e-Mail: afnn@rambler.ru;
^b G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, Tropinina Street 49, 603600 Nizhnii Novgorod, Russian Federation
e-Mail: andrew@imoc.sinn.ru;
^c Department of Chemistry, M.V. Lomonosov State University, Leninskie Gori, 119992 Moscow, Russian Federation
e-Mail: beletska@org.chem.msu.ru;
^d Department Chemie and Biochemie, Ludwig Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 München, Germany
e-Mail: gavch@cup.uni-muenchen.de;
^e UMR 6264, Faculte des Sciences Saint-Jerome, Universite d’Aix Marseille 1 et 2, 13397 Marseille Cedex 20, France
e-Mail: Sebastien.Combes@univ-provence.fr;

Abstract

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Abstract

Several 2-(azidomethyl)arylboronic acids were synthesized. Their involvement into organolead-mediated Pinhey arylation reaction with 4-hydroxycoumarins afforded 3-[2-(azidomethyl)aryl]-4-hydroxycoumarins or [4,3-c]isoquinolinocoumarins in reasonable yields via two- or four-step one-pot reaction sequence. Palladium-catalyzed cross-coupling of organoboron reagents with 4-trifluoromethylsulfonyloxycoumarins under Suzuki reaction conditions gave 4-[2-(azidomethyl)aryl]coumarins in good yields. 2-(Azidomethyl)arylboronic acid, as well as azide-containing iso- and neoflavonoid compounds underwent catalytic alkyne-azide cycloaddition in THF-water, providing 1,4-triazole compounds regioselectively in good to excellent yields.

Key words

coumarins - azides - arylation - cross-coupling - cycloaddition

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