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Synthesis 2010(3): 470-476  
DOI: 10.1055/s-0029-1217133
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile [2+2] Cycloaddition of DDQ to an Alkyne: Synthesis of Pyrrolyl- and Indolylbicyclo[4.2.0]octadienes from C-Ethynylpyrroles or C-Ethynylindoles

Boris A. Trofimov*, Lyubov’ N. Sobenina, Zinaida V. Stepanova, Igor’ A. Ushakov, Lidiya M. Sinegovskaya, Tamara I. Vakul’skaya, Al’bina I. Mikhaleva
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;
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Publication History

Received 23 September 2009
Publication Date:
20 November 2009 (online)

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Abstract

C-Ethynylpyrroles or -indoles, which can be prepared by cross-coupling of pyrroles or indoles with haloalkynes on active surfaces, undergo [2+2]-cycloaddition reactions with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to give 2-pyrrolyl- or 3-indolylbicyclooctadienes in almost quantitative yields. The adducts are charge-transfer complexes that are paramagnetic in the solid state, and therefore represent a new family of densely functionalized pyrrole and indole derivatives potentially useful as pharmaceutical candidates, highly potent building blocks, or precursors of advanced materials. The reaction contributes to the practical and basic chemistry of pyrroles, indoles, alkynes, and quinones.

Key words

pyrroles - indoles - cycloadditions - alkynes - polycycles

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