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Synthesis 2009(10): 1673-1682  
DOI: 10.1055/s-0028-1088058
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Mikael I. Naumova, Alexander V. Nucheva, Nikolay S. Sitnikova, Yulia B. Malyshevaa, Andrew S. Shavyrinb, Irina P. Beletskayac, Andrei E. Gavryushind, Sebastien Combese, 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;
Further Information

Publication History

Received 9 December 2008
Publication Date:
20 April 2009 (online)

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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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38

Boronic acids 21a-c, like their precursors 4a,b coexist with anhydride forms of boronic acids with different degree of oligomerization. The NMR spectra of 21a-c derivatives purified by crystallization were rather complicated. On the other hand, when compounds 21a-c were isolated by column chromatography on silica gel, the NMR spectra of these products became almost fine due to the cleavage of the ether bonds in the associates.